Miconazole nitrate vag supp usp 200 mg

Summary

Miconazole is an azole antifungal with broad-spectrum activity used to treat fungal infections affecting the vagina, mouth and skin, including candidiasis.

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Miconazole is a broad-spectrum azole antifungal with some activity against Gram-positive bacteria as well.3 It is widely used to treat mucosal yeast infections, including both oral and vaginal infections; although intravenous miconazole is no longer available, a wide variety of suppositories, creams, gels, and tablet-based products are available.13,14,15,16,17 Miconazole is thought to act primarily through the inhibition of fungal CYP450 14α-lanosterol demethylase activity.3,4

Miconazole was first synthesized in 1969 and first granted FDA approval on January 8, 1974, for sale by INSIGHT Pharmaceuticals as a topical cream.12,13 It is currently available as a variety of prescription and over the counter products. Despite having been in clinical use for an extended period, resistance to miconazole among susceptible organisms is relatively low.3

• 1-(2,4-Dichloro-beta-((2,4-dichlorobenzyl)oxy)phenethyl)imidazole
• 1-[2-(2,4-Dichloro-benzyloxy)-2-(2,4-dichloro-phenyl)-ethyl]-1H-imidazole
• Miconazol
• Miconazole
• Miconazolum

• MJR 1762
• R 18134

Miconazole is indicated for the local treatment of oropharyngeal candidiasis in adult patients and for the adjunctive treatment of diaper dermatitis complicated by candidiasis in immunocompetent patients aged four weeks and older.13,14 Miconazole is available as both a suppository and cream for the treatment of vaginal yeast infections and the relief of associated vulvar itching and irritation.15 Lastly, miconazole cream is effective in treating athlete's foot (tinea pedis), jock itch (tinea cruris), ringworm infections (tinea corporis),16 pityriasis (formerly tinea) versicolor,2 and cutaneous candidiasis.1

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• Acne Vulgaris
• Dermatophytosis
• Dermatophytosis of nail
• Diaper Dermatitis
• Excessive sweating and body odor
• Fungal skin infection
• Gastrointestinal candidiasis
• Infection, Mixed
• Infections, Fungal of the Skin Folds
• Nail candida
• Oropharyngeal Candidiasis
• Pityriasis versicolor
• Ringworm
• Seborrheic Dermatitis
• Skin candida
• Tinea Capitis
• Tinea Corporis
• Tinea Cruris
• Tinea Pedis
• Vaginal Candidiasis
• Cutaneous candidiasis

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Miconazole is an azole antifungal that functions primarily through inhibition of a specific demethylase within the CYP450 complex.3 As miconazole is typically applied topically and is minimally absorbed into the systemic circulation following application, the majority of patient reactions are limited to hypersensitivity and cases of anaphylaxis.13 Patients using intravaginal miconazole products are advised not to rely on contraceptives to prevent pregnancy and sexually transmitted infections, as well as not to use tampons concurrently.15

Miconazole is an azole antifungal used to treat a variety of conditions, including those caused by Candida overgrowth. Unique among the azoles, miconazole is thought to act through three main mechanisms.3 The primary mechanism of action is through inhibition of the CYP450 14α-lanosterol demethylase enzyme, which results in altered ergosterol production and impaired cell membrane composition and permeability, which in turn leads to cation, phosphate, and low molecular weight protein leakage.3,4

In addition, miconazole inhibits fungal peroxidase and catalase while not affecting NADH oxidase activity, leading to increased production of reactive oxygen species (ROS).3,4,5 Increased intracellular ROS leads to downstream pleiotropic effects and eventual apoptosis.3

Lastly, likely as a result of lanosterol demethylation inhibition, miconazole causes a rise in intracellular levels of farnesol. This molecule participates in quorum sensing in Candida, preventing the transition from yeast to mycelial forms and thereby the formation of biofilms, which are more resistant to antibiotics.6,7 In addition, farnesol is an inhibitor of drug efflux ABC transporters, namely Candida CaCdr1p and CaCdr2p, which may additionally contribute to increased effectiveness of azole drugs.7

Miconazole given to healthy volunteers as a single 50 mg oral tablet produced a mean Cmax of 15.1 ± 16.2 mcg/mL, a mean AUC0-24 of 55.2 ± 35.1 mcg*h/mL, and a median Tmax of 7 hours (range 2.0-24.1). In these patients measurable plasma concentrations ranged from 0.5 to 0.83 mcg/mL.13

Topical miconazole is absorbed poorly into the systemic circulation.3 In pediatric patients aged 1-21 months given multiple topical applications of miconazole ointment for seven days, the plasma miconazole concentration was less than 0.5 ng/mL in 88% of the patients, with the remaining patients having a concentration of 0.57 and 0.58 ng/mL, respectively.14 Similarly, patients. administered with a vaginal 1200 mg ovule had a mean Cmax of 10.71 ng/mL, mean Tmax of 18.4 hours, and mean AUC0-96 of 477.3 ng*h/mL.9

A 1200 mg miconazole vaginal suppository resulted in a calculated apparent volume of distribution of 95 546 L while a 100 mg vaginal cream yielded an apparent volume of distribution of 10 911L.9

In vitro data suggests that miconazole binds human serum albumin, however, the clinical significance of this observation is unclear.10,11

Miconazole is metabolized in the liver and does not give rise to any active metabolites.13

Miconazole is excreted through both urine and feces; less than 1% of unchanged miconazole is recovered in urine.13

Miconazole has a terminal half-life of 24 hours.13

Not Available

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Miconazole overdose has not been reported.13 Patients experiencing an overdose are at an increased risk of severe adverse effects such as headache, skin irritation, diarrhea, nausea, vomiting, abdominal pain, and dysgeusia. Symptomatic and supportive measures are recommended.

Miconazole has an oral LD50 of 500 mg/kg in rats.MSDS

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

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Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Monistat 3	Suppository	200 mg/1	Vaginal	ORTHO PHARMACEUTICAL CORPORATION	2006-12-31	Not applicable
Monistat-derm	Cream	20 mg/1g	Topical	Ortho-McNeil Pharmaceutical, Inc.	2006-10-02	Not applicable
Oravig	Tablet	50 mg/1	Buccal	Par Pharmaceuticals Companies, Inc.	2010-04-26	2013-06-10
Oravig	Tablet	50 mg/1	Buccal	Galt Pharmaceuticals, LLC	2021-12-31	Not applicable
Oravig	Tablet	50 mg/1	Buccal	Midatech Pharma Us, Inc.	2010-04-16	Not applicable
Oravig	Tablet	50 mg/1	Buccal	Praelia Pharmaceuticals Inc	2012-11-01	2015-09-30

• A07AC — Imidazole derivatives
• A07A — INTESTINAL ANTIINFECTIVES
• A07 — ANTIDIARRHEALS, INTESTINAL ANTIINFLAMMATORY/ANTIINFECTIVE AGENTS
• A — ALIMENTARY TRACT AND METABOLISM

• J02AB — Imidazole derivatives
• J02A — ANTIMYCOTICS FOR SYSTEMIC USE
• J02 — ANTIMYCOTICS FOR SYSTEMIC USE
• J — ANTIINFECTIVES FOR SYSTEMIC USE

• D01AC — Imidazole and triazole derivatives
• D01A — ANTIFUNGALS FOR TOPICAL USE
• D01 — ANTIFUNGALS FOR DERMATOLOGICAL USE
• D — DERMATOLOGICALS

• G01AF — Imidazole derivatives
• G01A — ANTIINFECTIVES AND ANTISEPTICS, EXCL. COMBINATIONS WITH CORTICOSTEROIDS
• G01 — GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS
• G — GENITO URINARY SYSTEM AND SEX HORMONES

• A01AB — Antiinfectives and antiseptics for local oral treatment
• A01A — STOMATOLOGICAL PREPARATIONS
• A01 — STOMATOLOGICAL PREPARATIONS
• A — ALIMENTARY TRACT AND METABOLISM

• D01AC — Imidazole and triazole derivatives
• D01A — ANTIFUNGALS FOR TOPICAL USE
• D01 — ANTIFUNGALS FOR DERMATOLOGICAL USE
• D — DERMATOLOGICALS

• S02AA — Antiinfectives
• S02A — ANTIINFECTIVES
• S02 — OTOLOGICALS
• S — SENSORY ORGANS

• G01AF — Imidazole derivatives
• G01A — ANTIINFECTIVES AND ANTISEPTICS, EXCL. COMBINATIONS WITH CORTICOSTEROIDS
• G01 — GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS
• G — GENITO URINARY SYSTEM AND SEX HORMONES

• 14-alpha Demethylase Inhibitors
• Anti-Infective Agents
• Antifungal Agents
• Antifungal Agents (Vaginal)
• Antifungals for Dermatological Use
• Antifungals for Topical Use
• Antiinfectives and Antiseptics for Local Oral Treatment
• Azole Antifungals
• Chemically-Induced Disorders
• Cytochrome P-450 CYP2A6 Inhibitors
• Cytochrome P-450 CYP2A6 Inhibitors (strong)
• Cytochrome P-450 CYP2B6 Inhibitors
• Cytochrome P-450 CYP2B6 Inhibitors (strength unknown)
• Cytochrome P-450 CYP2C19 Inhibitors
• Cytochrome P-450 CYP2C19 inhibitors (strength unknown)
• Cytochrome P-450 CYP2C19 Inhibitors (strong)
• Cytochrome P-450 CYP2C8 Inhibitors
• Cytochrome P-450 CYP2C8 Inhibitors (strength unknown)
• Cytochrome P-450 CYP2C9 Inhibitors
• Cytochrome P-450 CYP2C9 Inhibitors (moderate)
• Cytochrome P-450 CYP2C9 Inhibitors (strong)
• Cytochrome P-450 CYP2D6 Inhibitors
• Cytochrome P-450 CYP2D6 Inhibitors (strength unknown)
• Cytochrome P-450 CYP2E1 Inhibitors
• Cytochrome P-450 CYP2E1 Inhibitors (strong)
• Cytochrome P-450 CYP3A Inhibitors
• Cytochrome P-450 CYP3A4 Inhibitors
• Cytochrome P-450 CYP3A4 Inhibitors (moderate)
• Cytochrome P-450 Enzyme Inhibitors
• Dermatologicals
• Enzyme Inhibitors
• Genito Urinary System and Sex Hormones
• Gynecological Antiinfectives and Antiseptics
• Hormone Antagonists
• Hormones, Hormone Substitutes, and Hormone Antagonists
• Imidazole and Triazole Derivatives
• Imidazole Derivatives
• Imidazoles
• Intestinal Antiinfectives
• Otologicals
• P-glycoprotein inhibitors
• Sensory Organs
• Steroid Synthesis Inhibitors
• Stomatological Preparations
• Vaginal Creams, Foams, and Jellies

• Fungi, yeast and protozoans

InChI=1S/C18H14Cl4N2O/c19-13-2-1-12(16(21)7-13)10-25-18(9-24-6-5-23-11-24)15-4-3-14(20)8-17(15)22/h2-8,11,18H,9-10H2

1-[2-(2,4-dichlorophenyl)-2-[(2,4-dichlorophenyl)methoxy]ethyl]-1H-imidazole

ClC1=CC(Cl)=C(COC(CN2C=CN=C2)C2=C(Cl)C=C(Cl)C=C2)C=C1

1. Taudorf EH, Jemec GBE, Hay RJ, Saunte DML: Cutaneous candidiasis - an evidence-based review of topical and systemic treatments to inform clinical practice. J Eur Acad Dermatol Venereol. 2019 Oct;33(10):1863-1873. doi: 10.1111/jdv.15782. Epub 2019 Jul 30. [Article]
2. Tanenbaum L, Anderson C, Rosenberg MJ, Akers W: 1% sulconazole cream v 2% miconazole cream in the treatment of tinea versicolor. A double-blind, multicenter study. Arch Dermatol. 1984 Feb;120(2):216-9. [Article]
3. Pierard GE, Hermanns-Le T, Delvenne P, Pierard-Franchimont C: Miconazole, a pharmacological barrier to skin fungal infections. Expert Opin Pharmacother. 2012 Jun;13(8):1187-94. doi: 10.1517/14656566.2012.687047. Epub 2012 May 8. [Article]
4. De Nollin S, Borgers M: An ultrastructural and cytochemical study of Candida albicans after in vitro treatment with imidazoles. Mykosen. 1976 Sep;19(9):317-28. doi: 10.1111/j.1439-0507.1976.tb01469.x. [Article]
5. Kobayashi D, Kondo K, Uehara N, Otokozawa S, Tsuji N, Yagihashi A, Watanabe N: Endogenous reactive oxygen species is an important mediator of miconazole antifungal effect. Antimicrob Agents Chemother. 2002 Oct;46(10):3113-7. doi: 10.1128/aac.46.10.3113-3117.2002. [Article]
6. Hornby JM, Nickerson KW: Enhanced production of farnesol by Candida albicans treated with four azoles. Antimicrob Agents Chemother. 2004 Jun;48(6):2305-7. doi: 10.1128/AAC.48.6.2305-2307.2004. [Article]
7. Sharma M, Prasad R: The quorum-sensing molecule farnesol is a modulator of drug efflux mediated by ABC multidrug transporters and synergizes with drugs in Candida albicans. Antimicrob Agents Chemother. 2011 Oct;55(10):4834-43. doi: 10.1128/AAC.00344-11. Epub 2011 Jul 18. [Article]
8. Thevissen K, Ayscough KR, Aerts AM, Du W, De Brucker K, Meert EM, Ausma J, Borgers M, Cammue BP, Francois IE: Miconazole induces changes in actin cytoskeleton prior to reactive oxygen species induction in yeast. J Biol Chem. 2007 Jul 27;282(30):21592-7. doi: 10.1074/jbc.M608505200. Epub 2007 Jun 6. [Article]
9. Stevens RE, Konsil J, Verrill SS, Roy P, Desai PB, Upmalis DH, Cone FL: Bioavailability study of a 1200 mg miconazole nitrate vaginal ovule in healthy female adults. J Clin Pharmacol. 2002 Jan;42(1):52-60. doi: 10.1177/0091270002042001006. [Article]
10. Schafer-Korting M, Korting HC, Rittler W, Obermuller W: Influence of serum protein binding on the in vitro activity of anti-fungal agents. Infection. 1995 Sep-Oct;23(5):292-7. doi: 10.1007/bf01716289. [Article]
11. Hu Z, Zhang J, Cheng X: Antifungal efficiency of miconazole and econazole and the interaction with transport protein: a comparative study. Pharm Biol. 2015 Feb;53(2):251-61. doi: 10.3109/13880209.2014.914232. Epub 2014 Nov 7. [Article]
12. Godefroi EF, Heeres J, Van Cutsem J, Janssen PA: The preparation and antimycotic properties of derivatives of 1-phenethylimidazole. J Med Chem. 1969 Sep;12(5):784-91. doi: 10.1021/jm00305a014. [Article]
13. FDA Approved Drug Products: Oravig (miconazole) buccal tablet [Link]
14. FDA Approved Drug Products: Vusion (miconazole nitrate, zinc oxide, white petrolatum) topical ointment [Link]
15. FDA Approved Drug Products: miconazole nitrate suppositories and cream [Link]
16. DailyMed miconazole nitrate [Link]
17. FDA Approved Drug Products: Monistat (miconazole nitrate) suppositories and cream [Link]
18. AIFA Product Information: Nizacol (miconazole) oral tablets [Link]

Not Available

• Actavis Group
• Advanced Pharmaceutical Services Inc.
• Barr Pharmaceuticals
• CVS Pharmacy
• Dispensing Solutions
• Diversified Healthcare Services Inc.
• Draxis Specialty Pharmaceuticals Inc.
• Ivax Pharmaceuticals
• Johnson & Johnson Healthcare
• Kaiser Foundation Hospital
• Medisca Inc.
• Ortho Mcneil Janssen Pharmaceutical Inc.
• Orthopedics Advanced Care
• Par Pharmaceuticals
• Perrigo Co.
• Pharmacia Inc.
• Pharmedix
• Physicians Total Care Inc.
• Prescript Pharmaceuticals
• Schering-Plough Inc.
• Southwood Pharmaceuticals

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ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

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KindProteinOrganismYeastPharmacological action

Yes

Inhibitor

General FunctionSterol 14-demethylase activitySpecific FunctionCatalyzes C14-demethylation of lanosterol which is critical for ergosterol biosynthesis. It transforms lanosterol into 4,4'-dimethyl cholesta-8,14,24-triene-3-beta-ol.Gene NameERG11Uniprot IDP10613Uniprot NameLanosterol 14-alpha demethylaseMolecular Weight60674.965 Da

References

1. White TC, Marr KA, Bowden RA: Clinical, cellular, and molecular factors that contribute to antifungal drug resistance. Clin Microbiol Rev. 1998 Apr;11(2):382-402. [Article]
2. Ghannoum MA, Rice LB: Antifungal agents: mode of action, mechanisms of resistance, and correlation of these mechanisms with bacterial resistance. Clin Microbiol Rev. 1999 Oct;12(4):501-17. [Article]
3. Edlind T, Smith L, Henry K, Katiyar S, Nickels J: Antifungal activity in Saccharomyces cerevisiae is modulated by calcium signalling. Mol Microbiol. 2002 Oct;46(1):257-68. [Article]
4. Georgopapadakou NH, Walsh TJ: Antifungal agents: chemotherapeutic targets and immunologic strategies. Antimicrob Agents Chemother. 1996 Feb;40(2):279-91. [Article]

Kind ProteinOrganismHumansPharmacological action

Unknown

Inhibitor

General FunctionTetrahydrobiopterin bindingSpecific FunctionProduces nitric oxide (NO) which is implicated in vascular smooth muscle relaxation through a cGMP-mediated signal transduction pathway. NO mediates vascular endothelial growth factor (VEGF)-induce...Gene NameNOS3Uniprot IDP29474Uniprot NameNitric oxide synthase, endothelialMolecular Weight133287.62 Da

References

1. Wolff DJ, Datto GA, Samatovicz RA: The dual mode of inhibition of calmodulin-dependent nitric-oxide synthase by antifungal imidazole agents. J Biol Chem. 1993 May 5;268(13):9430-6. [Article]
2. Bogle RG, Whitley GS, Soo SC, Johnstone AP, Vallance P: Effect of anti-fungal imidazoles on mRNA levels and enzyme activity of inducible nitric oxide synthase. Br J Pharmacol. 1994 Apr;111(4):1257-61. [Article]
3. Sennequier N, Wolan D, Stuehr DJ: Antifungal imidazoles block assembly of inducible NO synthase into an active dimer. J Biol Chem. 1999 Jan 8;274(2):930-8. [Article]
4. Dudek RR, Conforto A, Pinto V, Wildhirt S, Suzuki H: Inhibition of endothelial nitric oxide synthase by cytochrome P-450 reductase inhibitors. Proc Soc Exp Biol Med. 1995 May;209(1):60-4. [Article]

KindProteinOrganismHumansPharmacological action

Unknown

Inhibitor

General FunctionTetrahydrobiopterin bindingSpecific FunctionProduces nitric oxide (NO) which is a messenger molecule with diverse functions throughout the body. In macrophages, NO mediates tumoricidal and bactericidal actions. Also has nitrosylase activity ...Gene NameNOS2Uniprot IDP35228Uniprot NameNitric oxide synthase, inducibleMolecular Weight131116.3 Da

References

1. Wolff DJ, Datto GA, Samatovicz RA: The dual mode of inhibition of calmodulin-dependent nitric-oxide synthase by antifungal imidazole agents. J Biol Chem. 1993 May 5;268(13):9430-6. [Article]
2. Bogle RG, Whitley GS, Soo SC, Johnstone AP, Vallance P: Effect of anti-fungal imidazoles on mRNA levels and enzyme activity of inducible nitric oxide synthase. Br J Pharmacol. 1994 Apr;111(4):1257-61. [Article]
3. Sennequier N, Wolan D, Stuehr DJ: Antifungal imidazoles block assembly of inducible NO synthase into an active dimer. J Biol Chem. 1999 Jan 8;274(2):930-8. [Article]
4. Dudek RR, Conforto A, Pinto V, Wildhirt S, Suzuki H: Inhibition of endothelial nitric oxide synthase by cytochrome P-450 reductase inhibitors. Proc Soc Exp Biol Med. 1995 May;209(1):60-4. [Article]

KindProteinOrganism HumansPharmacological action

Unknown

Partial agonist

General FunctionZinc ion bindingSpecific FunctionNuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism an...Gene NameNR1I2Uniprot IDO75469Uniprot NameNuclear receptor subfamily 1 group I member 2Molecular Weight49761.245 Da

References

1. Svecova L, Vrzal R, Burysek L, Anzenbacherova E, Cerveny L, Grim J, Trejtnar F, Kunes J, Pour M, Staud F, Anzenbacher P, Dvorak Z, Pavek P: Azole antimycotics differentially affect rifampicin-induced pregnane X receptor-mediated CYP3A4 gene expression. Drug Metab Dispos. 2008 Feb;36(2):339-48. Epub 2007 Nov 12. [Article]

KindProtein groupOrganismHumansPharmacological action

Unknown

Inhibitor

General FunctionVoltage-gated potassium channel activitySpecific FunctionPotassium channel activated by both membrane depolarization or increase in cytosolic Ca(2+) that mediates export of K(+). It is also activated by the concentration of cytosolic Mg(2+). Its activati...

Components:

References

1. Hatton CJ, Peers C: Effects of cytochrome P-450 inhibitors on ionic currents in isolated rat type I carotid body cells. Am J Physiol. 1996 Jul;271(1 Pt 1):C85-92. [Article]
2. Alvarez J, Montero M, Garcia-Sancho J: High affinity inhibition of Ca(2+)-dependent K+ channels by cytochrome P-450 inhibitors. J Biol Chem. 1992 Jun 15;267(17):11789-93. [Article]

KindProtein groupOrganismNot AvailablePharmacological action

Unknown

Inhibitor

General FunctionVoltage-gated potassium channel activitySpecific FunctionVoltage-gated potassium channel that mediates transmembrane potassium transport in excitable membranes, primarily in the brain and the central nervous system, but also in the kidney (PubMed:1990381...

Components:

References

1. Hatton CJ, Peers C: Effects of cytochrome P-450 inhibitors on ionic currents in isolated rat type I carotid body cells. Am J Physiol. 1996 Jul;271(1 Pt 1):C85-92. [Article]
2. Kikuchi K, Nagatomo T, Abe H, Kawakami K, Duff HJ, Makielski JC, January CT, Nakashima Y: Blockade of HERG cardiac K+ current by antifungal drug miconazole. Br J Pharmacol. 2005 Mar;144(6):840-8. [Article]
3. Sung DJ, Kim JG, Won KJ, Kim B, Shin HC, Park JY, Bae YM: Blockade of K+ and Ca2+ channels by azole antifungal agents in neonatal rat ventricular myocytes. Biol Pharm Bull. 2012;35(9):1469-75. doi: 10.1248/bpb.b12-00002. [Article]

KindProtein groupOrganismHumansPharmacological action

Unknown

Inhibitor

General FunctionInward rectifier potassium channel activitySpecific FunctionInward rectifying potassium channel that is activated by phosphatidylinositol 4,5-bisphosphate and that probably participates in controlling the resting membrane potential in electrically excitable...

Components:

References

1. Sung DJ, Kim JG, Won KJ, Kim B, Shin HC, Park JY, Bae YM: Blockade of K+ and Ca2+ channels by azole antifungal agents in neonatal rat ventricular myocytes. Biol Pharm Bull. 2012;35(9):1469-75. doi: 10.1248/bpb.b12-00002. [Article]

KindProtein groupOrganismHumansPharmacological action

Unknown

Inhibitor

General FunctionVoltage-gated calcium channel activitySpecific FunctionVoltage-sensitive calcium channels (VSCC) mediate the entry of calcium ions into excitable cells and are also involved in a variety of calcium-dependent processes, including muscle contraction, hor...

Components:

References

1. Sung DJ, Kim JG, Won KJ, Kim B, Shin HC, Park JY, Bae YM: Blockade of K+ and Ca2+ channels by azole antifungal agents in neonatal rat ventricular myocytes. Biol Pharm Bull. 2012;35(9):1469-75. doi: 10.1248/bpb.b12-00002. [Article]

Enzymes

KindProteinOrganism HumansPharmacological action

Unknown

Inhibitor

General FunctionSteroid hydroxylase activitySpecific FunctionCytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...Gene NameCYP2C9Uniprot IDP11712Uniprot NameCytochrome P450 2C9Molecular Weight55627.365 Da

References

1. Niwa T, Shiraga T, Takagi A: Effect of antifungal drugs on cytochrome P450 (CYP) 2C9, CYP2C19, and CYP3A4 activities in human liver microsomes. Biol Pharm Bull. 2005 Sep;28(9):1805-8. [Article]
2. Venkatakrishnan K, von Moltke LL, Greenblatt DJ: Effects of the antifungal agents on oxidative drug metabolism: clinical relevance. Clin Pharmacokinet. 2000 Feb;38(2):111-80. doi: 10.2165/00003088-200038020-00002. [Article]
3. Niwa T, Imagawa Y, Yamazaki H: Drug interactions between nine antifungal agents and drugs metabolized by human cytochromes P450. Curr Drug Metab. 2014;15(7):651-79. [Article]
4. Monostory K, Hazai E, Vereczkey L: Inhibition of cytochrome P450 enzymes participating in p-nitrophenol hydroxylation by drugs known as CYP2E1 inhibitors. Chem Biol Interact. 2004 Apr 15;147(3):331-40. doi: 10.1016/j.cbi.2004.03.003. [Article]
5. Flockhart Table of Drug Interactions [Link]
6. FDA Drug Development and Drug Interactions: Table of Substrates, Inhibitors and Inducers [Link]

KindProteinOrganismHumansPharmacological action

Unknown

Inhibitor

General FunctionSteroid hydroxylase activitySpecific FunctionResponsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...Gene NameCYP2C19Uniprot IDP33261Uniprot Name Cytochrome P450 2C19Molecular Weight55930.545 Da

References

1. Niwa T, Shiraga T, Takagi A: Effect of antifungal drugs on cytochrome P450 (CYP) 2C9, CYP2C19, and CYP3A4 activities in human liver microsomes. Biol Pharm Bull. 2005 Sep;28(9):1805-8. [Article]
2. Zhang W, Ramamoorthy Y, Kilicarslan T, Nolte H, Tyndale RF, Sellers EM: Inhibition of cytochromes P450 by antifungal imidazole derivatives. Drug Metab Dispos. 2002 Mar;30(3):314-8. [Article]
3. Monostory K, Hazai E, Vereczkey L: Inhibition of cytochrome P450 enzymes participating in p-nitrophenol hydroxylation by drugs known as CYP2E1 inhibitors. Chem Biol Interact. 2004 Apr 15;147(3):331-40. doi: 10.1016/j.cbi.2004.03.003. [Article]
4. Flockhart Table of Drug Interactions [Link]
5. FDA Drug Development and Drug Interactions: Table of Substrates, Inhibitors and Inducers [Link]

KindProteinOrganismHumansPharmacological action

Unknown

Inhibitor

General FunctionSteroid hydroxylase activitySpecific FunctionExhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Const...Gene NameCYP2A6Uniprot IDP11509Uniprot Name Cytochrome P450 2A6Molecular Weight56501.005 Da

References

1. Draper AJ, Madan A, Parkinson A: Inhibition of coumarin 7-hydroxylase activity in human liver microsomes. Arch Biochem Biophys. 1997 May 1;341(1):47-61. doi: 10.1006/abbi.1997.9964. [Article]
2. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [Article]
3. Venkatakrishnan K, von Moltke LL, Greenblatt DJ: Effects of the antifungal agents on oxidative drug metabolism: clinical relevance. Clin Pharmacokinet. 2000 Feb;38(2):111-80. doi: 10.2165/00003088-200038020-00002. [Article]

KindProteinOrganismHumansPharmacological action

Unknown

Inhibitor

General FunctionSteroid hydroxylase activitySpecific FunctionMetabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic ...Gene NameCYP2E1Uniprot IDP05181Uniprot NameCytochrome P450 2E1Molecular Weight56848.42 Da

References

1. Niwa T, Inoue-Yamamoto S, Shiraga T, Takagi A: Effect of antifungal drugs on cytochrome P450 (CYP) 1A2, CYP2D6, and CYP2E1 activities in human liver microsomes. Biol Pharm Bull. 2005 Sep;28(9):1813-6. [Article]
2. Zhang W, Ramamoorthy Y, Kilicarslan T, Nolte H, Tyndale RF, Sellers EM: Inhibition of cytochromes P450 by antifungal imidazole derivatives. Drug Metab Dispos. 2002 Mar;30(3):314-8. [Article]
3. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [Article]
4. Tassaneeyakul W, Birkett DJ, Miners JO: Inhibition of human hepatic cytochrome P4502E1 by azole antifungals, CNS-active drugs and non-steroidal anti-inflammatory agents. Xenobiotica. 1998 Mar;28(3):293-301. doi: 10.1080/004982598239579 . [Article]
5. Flockhart Table of Drug Interactions [Link]

KindProteinOrganismHumansPharmacological action

Unknown

Inhibitor

General FunctionVitamin d3 25-hydroxylase activitySpecific FunctionCytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react... Gene NameCYP3A4Uniprot IDP08684Uniprot NameCytochrome P450 3A4Molecular Weight57342.67 Da

References

1. Sakaeda T, Iwaki K, Kakumoto M, Nishikawa M, Niwa T, Jin JS, Nakamura T, Nishiguchi K, Okamura N, Okumura K: Effect of micafungin on cytochrome P450 3A4 and multidrug resistance protein 1 activities, and its comparison with azole antifungal drugs. J Pharm Pharmacol. 2005 Jun;57(6):759-64. [Article]
2. Monostory K, Hazai E, Vereczkey L: Inhibition of cytochrome P450 enzymes participating in p-nitrophenol hydroxylation by drugs known as CYP2E1 inhibitors. Chem Biol Interact. 2004 Apr 15;147(3):331-40. doi: 10.1016/j.cbi.2004.03.003. [Article]
3. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [Article]
4. Zhang W, Ramamoorthy Y, Kilicarslan T, Nolte H, Tyndale RF, Sellers EM: Inhibition of cytochromes P450 by antifungal imidazole derivatives. Drug Metab Dispos. 2002 Mar;30(3):314-8. [Article]
5. Niwa T, Imagawa Y, Yamazaki H: Drug interactions between nine antifungal agents and drugs metabolized by human cytochromes P450. Curr Drug Metab. 2014;15(7):651-79. [Article]
6. Flockhart Table of Drug Interactions [Link]
7. FDA Drug Development and Drug Interactions: Table of Substrates, Inhibitors and Inducers [Link]
8. FDA Approved Drug Products: Oravig (miconazole) buccal tablet [Link]

KindProteinOrganismHumansPharmacological action

Unknown

Inhibitor

General FunctionSteroid hydroxylase activitySpecific FunctionCytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...Gene NameCYP2B6Uniprot IDP20813Uniprot NameCytochrome P450 2B6 Molecular Weight56277.81 Da

References

1. Zhang W, Ramamoorthy Y, Kilicarslan T, Nolte H, Tyndale RF, Sellers EM: Inhibition of cytochromes P450 by antifungal imidazole derivatives. Drug Metab Dispos. 2002 Mar;30(3):314-8. [Article]
2. Flockhart Table of Drug Interactions [Link]
3. FDA Drug Development and Drug Interactions: Table of Substrates, Inhibitors and Inducers [Link]
4. Potential CYP2B6 Substrates, Inhibitors, Inudcers (https://ctep.cancer.gov/protocoldevelopment/docs/cyp2b6.doc) [File]

KindProteinOrganismHumansPharmacological action

Unknown

Inhibitor

General FunctionSteroid hydroxylase activitySpecific FunctionResponsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...Gene NameCYP2D6Uniprot IDP10635Uniprot NameCytochrome P450 2D6Molecular Weight55768.94 Da

References

1. Niwa T, Inoue-Yamamoto S, Shiraga T, Takagi A: Effect of antifungal drugs on cytochrome P450 (CYP) 1A2, CYP2D6, and CYP2E1 activities in human liver microsomes. Biol Pharm Bull. 2005 Sep;28(9):1813-6. [Article]
2. Zhang W, Ramamoorthy Y, Kilicarslan T, Nolte H, Tyndale RF, Sellers EM: Inhibition of cytochromes P450 by antifungal imidazole derivatives. Drug Metab Dispos. 2002 Mar;30(3):314-8. [Article]
3. Flockhart Table of Drug Interactions [Link]
4. FDA Drug Development and Drug Interactions: Table of Substrates, Inhibitors and Inducers [Link]

KindProteinOrganismHumans Pharmacological action

Unknown

Inhibitor

General FunctionSteroid hydroxylase activitySpecific FunctionCytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un... Gene NameCYP2C8Uniprot IDP10632Uniprot NameCytochrome P450 2C8Molecular Weight55824.275 Da

References

1. Niwa T, Imagawa Y: Substrate Specificity of Human Cytochrome P450 (CYP) 2C Subfamily and Effect of Azole Antifungal Agents on CYP2C8. J Pharm Pharm Sci. 2016 Oct - Dec;19(4):423-429. doi: 10.18433/J31S53. [Article]

KindProteinOrganismHumansPharmacological action

Unknown

Inhibitor

General FunctionSteroid 11-beta-monooxygenase activitySpecific FunctionHas steroid 11-beta-hydroxylase activity. In addition to this activity, the 18 or 19-hydroxylation of steroids and the aromatization of androstendione to estrone have also been ascribed to cytochro...Gene NameCYP11B1Uniprot IDP15538Uniprot NameCytochrome P450 11B1, mitochondrialMolecular Weight57572.44 Da

References

1. Denner K, Vogel R, Schmalix W, Doehmer J, Bernhardt R: Cloning and stable expression of the human mitochondrial cytochrome P45011B1 cDNA in V79 Chinese hamster cells and their application for testing of potential inhibitors. Pharmacogenetics. 1995 Apr;5(2):89-96. [Article]
2. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [Article]

KindProteinOrganismHumansPharmacological action

Unknown

Inhibitor

General FunctionSterol 14-demethylase activitySpecific FunctionCatalyzes C14-demethylation of lanosterol; it transforms lanosterol into 4,4'-dimethyl cholesta-8,14,24-triene-3-beta-ol.Gene NameCYP51A1 Uniprot IDQ16850Uniprot NameLanosterol 14-alpha demethylaseMolecular Weight56805.26 Da

References

1. Trosken ER, Scholz K, Lutz RW, Volkel W, Zarn JA, Lutz WK: Comparative assessment of the inhibition of recombinant human CYP19 (aromatase) by azoles used in agriculture and as drugs for humans. Endocr Res. 2004 Aug;30(3):387-94. [Article]
2. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [Article]

KindProtein OrganismHumansPharmacological action

Unknown

Inhibitor

General FunctionOxygen bindingSpecific FunctionCatalyzes the formation of aromatic C18 estrogens from C19 androgens.Gene NameCYP19A1Uniprot IDP11511Uniprot NameAromataseMolecular Weight57882.48 Da

References

1. Trosken ER, Scholz K, Lutz RW, Volkel W, Zarn JA, Lutz WK: Comparative assessment of the inhibition of recombinant human CYP19 (aromatase) by azoles used in agriculture and as drugs for humans. Endocr Res. 2004 Aug;30(3):387-94. [Article]

Carriers

KindProteinOrganismHumansPharmacological action

Unknown

Binder

General FunctionToxic substance bindingSpecific FunctionSerum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...Gene NameALBUniprot IDP02768Uniprot Name Serum albuminMolecular Weight69365.94 Da

References

1. Hu Z, Zhang J, Cheng X: Antifungal efficiency of miconazole and econazole and the interaction with transport protein: a comparative study. Pharm Biol. 2015 Feb;53(2):251-61. doi: 10.3109/13880209.2014.914232. Epub 2014 Nov 7. [Article]
2. Schafer-Korting M, Korting HC, Rittler W, Obermuller W: Influence of serum protein binding on the in vitro activity of anti-fungal agents. Infection. 1995 Sep-Oct;23(5):292-7. doi: 10.1007/bf01716289. [Article]

Transporters

KindProteinOrganismHumansPharmacological action

Unknown

Inhibitor

General FunctionXenobiotic-transporting atpase activitySpecific FunctionEnergy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.Gene NameABCB1Uniprot IDP08183Uniprot NameMultidrug resistance protein 1Molecular Weight141477.255 Da

References

1. Ekins S, Kim RB, Leake BF, Dantzig AH, Schuetz EG, Lan LB, Yasuda K, Shepard RL, Winter MA, Schuetz JD, Wikel JH, Wrighton SA: Three-dimensional quantitative structure-activity relationships of inhibitors of P-glycoprotein. Mol Pharmacol. 2002 May;61(5):964-73. [Article]
2. Schwab D, Fischer H, Tabatabaei A, Poli S, Huwyler J: Comparison of in vitro P-glycoprotein screening assays: recommendations for their use in drug discovery. J Med Chem. 2003 Apr 24;46(9):1716-25. [Article]
3. Yasuda K, Lan LB, Sanglard D, Furuya K, Schuetz JD, Schuetz EG: Interaction of cytochrome P450 3A inhibitors with P-glycoprotein. J Pharmacol Exp Ther. 2002 Oct;303(1):323-32. [Article]
4. Sakaeda T, Iwaki K, Kakumoto M, Nishikawa M, Niwa T, Jin JS, Nakamura T, Nishiguchi K, Okamura N, Okumura K: Effect of micafungin on cytochrome P450 3A4 and multidrug resistance protein 1 activities, and its comparison with azole antifungal drugs. J Pharm Pharmacol. 2005 Jun;57(6):759-64. [Article]

Drug created at June 13, 2005 13:24 / Updated at November 06, 2022 06:53

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