Methimazole
Identification
- Name
- Methimazole
- Accession Number
- DB00763 (APRD00002)
- Type
- Small Molecule
- Groups
- Approved
- Description
A thioureylene antithyroid agent that inhibits the formation of thyroid hormones by interfering with the incorporation of iodine into tyrosyl residues of thyroglobulin. This is done by interfering with the oxidation of iodide ion and iodotyrosyl groups through inhibition of the peroxidase enzyme.
- Structure
- Synonyms
- 1-Methylimidazole-2(3H)-thione
- Methimazole
- Thiamazol
- Thiamazole
- Thiamazolum
- Tiamazol
- External IDs
- NSC 38608 / USAF el-30
- Product Images
- Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Methimazole Tablet 10 mg/1 Oral United Research Laboratories, Inc. 2006-04-19 Not applicable US Methimazole Tablet 5 mg/1 Oral United Research Laboratories, Inc. 2006-04-19 Not applicable US Tapazole Tablet 10 mg Oral Paladin Labs Inc 2008-01-07 Not applicable Canada Tapazole Tablet 20 mg Oral Paladin Labs Inc Not applicable Not applicable Canada Tapazole 5mg Tablet Tablet 5 mg Oral Paladin Labs Inc 1951-12-31 Not applicable Canada - Generic Prescription Products
- International/Other Brands
- Danantizol (Gador S.A.) / Favistan (Temmler) / Metizol (ICN) / Strumazol (Organon) / Strumazole / Tapazole / Thacapzol (Recip) / Thycapzol (Sandoz) / Thyrozol (Merck) / Tirozol (Merck)
- Categories
- Cytochrome P-450 CYP1A2 Inhibitors
- Cytochrome P-450 CYP2A6 Inhibitors
- Cytochrome P-450 CYP2A6 Inhibitors (weak)
- Cytochrome P-450 CYP2B6 Inhibitors
- Cytochrome P-450 CYP2B6 Inhibitors (strong)
- Cytochrome P-450 CYP2C19 Inhibitors
- Cytochrome P-450 CYP2C9 Inhibitors
- Cytochrome P-450 CYP2D6 Inhibitors
- Cytochrome P-450 CYP2D6 Inhibitors (weak)
- Cytochrome P-450 CYP2E1 Inhibitors
- Cytochrome P-450 CYP2E1 Inhibitors (weak)
- Cytochrome P-450 CYP3A Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors (weak)
- Cytochrome P-450 Enzyme Inhibitors
- Hormone Antagonists
- Hormones, Hormone Substitutes, and Hormone Antagonists
- Imidazoles
- Immunosuppressive Agents
- Myelosuppressive Agents
- Sulfhydryl Compounds
- Sulfur Compounds
- Sulfur-Containing Imidazole Derivatives
- Systemic Hormonal Preparations, Excl. Sex Hormones and Insulins
- Thyroid Hormone Synthesis Inhibitor
- Thyroid Hormone Synthesis Inhibitors
- Thyroid Products
- UNII
- 554Z48XN5E
- CAS number
- 60-56-0
- Weight
- Average: 114.169
Monoisotopic: 114.025168892 - Chemical Formula
- C4H6N2S
- InChI Key
- PMRYVIKBURPHAH-UHFFFAOYSA-N
- InChI
- InChI=1S/C4H6N2S/c1-6-3-2-5-4(6)7/h2-3H,1H3,(H,5,7)
- IUPAC Name
- 1-methyl-2,3-dihydro-1H-imidazole-2-thione
- SMILES
- CN1C=CNC1=S
Pharmacology
- Indication
For the treatment of hyperthyroidism, goiter, Graves disease and psoriasis.
- Associated Conditions
- Pharmacodynamics
Used in the treatment of hyperthyroidism or an overactive thyroid gland, methimazole inhibits the synthesis of thyroid hormones and thus is effective in the treatment of hyperthyroidism. It may also be used to ameliorate hyperthyroidism in preparation for subtotal thyroidectomy or radioactive iodine therapy.
- Mechanism of action
Methimazole binds to thyroid peroxidase and thereby inhibits the conversion of iodide to iodine. Thyroid peroxidase normally converts iodide to iodine (via hydrogen peroxide as a cofactor) and also catalyzes the incorporation of the resulting iodide molecule onto both the 3 and/or 5 positions of the phenol rings of tyrosines found in thyroglobulin. Thyroglobulin is degraded to produce thyroxine (T4) and tri-iodothyronine (T3), which are the main hormones produced by the thyroid gland. So methimazole effectively inhibits the production of new thyroid hormones.
Target Actions Organism AThyroid peroxidase inhibitorHumans - Absorption
Rapid with an oral bioavailability of 93%.
- Volume of distribution
- Not Available
- Protein binding
None or minimal
- Metabolism
Primarily hepatic. Metabolized rapidly, requiring frequent administration.
- Route of elimination
Methimazole is excreted in the urine.
- Half life
5-6 hours
- Clearance
- Not Available
- Toxicity
Oral LD50 in rats is 2250 mg/kg. Symptoms of overdose include nausea, vomiting, epigastric distress, headache, fever, joint pain, pruritus, and edema. Aplastic anemia (pancy-topenia) or agranulocytosis may be manifested in hours to days. Less frequent events are hepatitis, nephrotic syndrome, exfoliative dermatitis, neuropathies, and CNS stimulation or depression.
- Affected organisms
- Humans and other mammals
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
Drug Interaction (R)-warfarin Methimazole may increase the anticoagulant activities of (R)-warfarin. (S)-Warfarin Methimazole may increase the anticoagulant activities of (S)-Warfarin. 2-Methoxyethanol The risk or severity of adverse effects can be increased when Methimazole is combined with 2-Methoxyethanol. 3-isobutyl-1-methyl-7H-xanthine The serum concentration of 3-isobutyl-1-methyl-7H-xanthine can be increased when it is combined with Methimazole. 3,5-diiodothyropropionic acid The metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Methimazole. 4-hydroxycoumarin The metabolism of 4-hydroxycoumarin can be decreased when combined with Methimazole. 4-Methoxyamphetamine The metabolism of 4-Methoxyamphetamine can be decreased when combined with Methimazole. 5-androstenedione The metabolism of 5-androstenedione can be decreased when combined with Methimazole. 6-O-benzylguanine The serum concentration of 6-O-benzylguanine can be increased when it is combined with Methimazole. 7-Deazaguanine The serum concentration of 7-Deazaguanine can be increased when it is combined with Methimazole. - Food Interactions
- Always take at the same moment in regard to meals, food may affect absorption unpredictably.
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0014901
- KEGG Drug
- D00401
- KEGG Compound
- C07190
- PubChem Compound
- 1349907
- PubChem Substance
- 46506536
- BindingDB
- 50241361
- ChEBI
- 50673
- ChEMBL
- CHEMBL1515
- Therapeutic Targets Database
- DNC001429
- PharmGKB
- PA450422
- HET
- MMZ
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Methimazole
- ATC Codes
- H03BB52 — Thiamazole, combinations
- H03BB — Sulfur-containing imidazole derivatives
- H03B — ANTITHYROID PREPARATIONS
- H03 — THYROID THERAPY
- H — SYSTEMIC HORMONAL PREPARATIONS, EXCL. SEX HORMONES AND INSULINS
- AHFS Codes
- 68:36.08 — Antithyroid Agents
- PDB Entries
- 2gvc / 4ig5 / 5ff1 / 5gsn
- MSDS
- Download (75.8 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 1, 2 Completed Treatment Graves´ Disease / Thyroid Associated Ophthalmopathy 1 2 Completed Treatment Dermatomyositis / Polymyositis 1 2 Terminated Supportive Care Glioblastoma Multiforme (GBM) 1 3 Recruiting Treatment Graves Diseases / Graves Ophthalmopathy / Graves' Ophthalmopathy Worsened 1 4 Completed Prevention Graves´ Disease 1 4 Completed Treatment Graves Diseases / Toxic Nodular Goitre 1 4 Completed Treatment Graves' Disease / Toxic Nodular Goitre 1 4 Unknown Status Diagnostic Healthy Volunteers 1 Not Available Completed Not Available Graves Diseases 1 Not Available Completed Treatment Graves Diseases 1 Not Available Completed Treatment Graves' Disease 1 Not Available Recruiting Not Available Gut Microbiota 1 Not Available Terminated Treatment Graves Ophthalmopathy 1
Pharmacoeconomics
- Manufacturers
- Actavis totowa llc
- Caraco pharmaceutical laboratories ltd
- Cedar pharmaceuticals llc
- Mylan pharmaceuticals inc
- Sandoz inc
- King pharmaceuticals inc
- King pharmaceuticals research and development inc sub king pharmaceuticals inc
- Packagers
- AAIPharma Inc.
- Actavis Group
- Amerisource Health Services Corp.
- Caraco Pharmaceutical Labs
- Cedar Pharmaceuticals LLC
- Centrix Pharmaceuticals
- Dispensing Solutions
- Eon Labs
- Heartland Repack Services LLC
- Kaiser Foundation Hospital
- King Pharmaceuticals Inc.
- Medisca Inc.
- Mikart Inc.
- Murfreesboro Pharmaceutical Nursing Supply
- Mylan
- Nucare Pharmaceuticals Inc.
- Par Pharmaceuticals
- Philopharm GmbH
- Physicians Total Care Inc.
- Remedy Repack
- Resource Optimization and Innovation LLC
- Southwood Pharmaceuticals
- United Research Laboratories Inc.
- Vangard Labs Inc.
- Dosage forms
Form Route Strength Tablet Oral 10 mg/1 Tablet Oral 5 mg/1 Tablet Oral 10 mg Tablet Oral 20 mg Tablet Oral 5 mg - Prices
Unit description Cost Unit Methimazole powder 9.49USD g Methimazole 20 mg tablet 1.9USD tablet Tapazole 10 mg tablet 1.45USD tablet Northyx 20 mg tablet 0.94USD tablet Northyx 15 mg tablet 0.82USD tablet Methimazole 10 mg tablet 0.78USD tablet Tapazole 5 mg tablet 0.66USD tablet Northyx 10 mg tablet 0.47USD tablet Methimazole 5 mg tablet 0.45USD tablet Northyx 5 mg tablet 0.29USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 146 °C PhysProp boiling point (°C) 280 °C PhysProp water solubility 275 g/L Not Available logP -0.34 HANSCH,C ET AL. (1995) - Predicted Properties
Property Value Source Water Solubility 11.3 mg/mL ALOGPS logP -0.38 ALOGPS logP 0.75 ChemAxon logS -1 ALOGPS pKa (Strongest Acidic) 10.41 ChemAxon pKa (Strongest Basic) -3 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 0 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 15.27 Å2 ChemAxon Rotatable Bond Count 0 ChemAxon Refractivity 33.23 m3·mol-1 ChemAxon Polarizability 11.64 Å3 ChemAxon Number of Rings 1 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter No ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET features
Property Value Probability Human Intestinal Absorption + 0.9156 Blood Brain Barrier + 0.9731 Caco-2 permeable + 0.6156 P-glycoprotein substrate Non-substrate 0.8213 P-glycoprotein inhibitor I Non-inhibitor 0.7552 P-glycoprotein inhibitor II Non-inhibitor 0.944 Renal organic cation transporter Non-inhibitor 0.7662 CYP450 2C9 substrate Non-substrate 0.7919 CYP450 2D6 substrate Non-substrate 0.8985 CYP450 3A4 substrate Non-substrate 0.7849 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.9232 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.8309 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.7105 Ames test Non AMES toxic 0.8582 Carcinogenicity Non-carcinogens 0.9348 Biodegradation Not ready biodegradable 0.9815 Rat acute toxicity 1.8215 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9401 hERG inhibition (predictor II) Non-inhibitor 0.8416
Spectra
- Mass Spec (NIST)
- Download (8.12 KB)
- Spectra
Taxonomy
- Description
- This compound belongs to the class of organic compounds known as imidazolethiones. These are aromatic compounds containing an imidazole ring which bears a thioketone group.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Azolines
- Sub Class
- Imidazolines
- Direct Parent
- Imidazolethiones
- Alternative Parents
- N-substituted imidazoles / Heteroaromatic compounds / Thioureas / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Hydrocarbon derivatives
- Substituents
- N-substituted imidazole / Imidazole-2-thione / Heteroaromatic compound / Imidazole / Azole / Thiourea / Azacycle / Organic nitrogen compound / Organopnictogen compound / Hydrocarbon derivative
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- imidazoles, thioureas (CHEBI:50673) / a small molecule (CPD-11282)
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Peroxidase activity
- Specific Function
- Iodination and coupling of the hormonogenic tyrosines in thyroglobulin to yield the thyroid hormones T(3) and T(4).
- Gene Name
- TPO
- Uniprot ID
- P07202
- Uniprot Name
- Thyroid peroxidase
- Molecular Weight
- 102961.63 Da
References
- Sugawara M, Sugawara Y, Wen K: Methimazole and propylthiouracil increase cellular thyroid peroxidase activity and thyroid peroxidase mRNA in cultured porcine thyroid follicles. Thyroid. 1999 May;9(5):513-8. [PubMed:10365684]
- Manzon RG, Holmes JA, Youson JH: Variable effects of goitrogens in inducing precocious metamorphosis in sea lampreys (Petromyzon marinus). J Exp Zool. 2001 Apr 15;289(5):290-303. [PubMed:11241400]
- Ferreira AC, de Carvalho Cardoso L, Rosenthal D, de Carvalho DP: Thyroid Ca2+/NADPH-dependent H2O2 generation is partially inhibited by propylthiouracil and methimazole. Eur J Biochem. 2003 Jun;270(11):2363-8. [PubMed:12755690]
- Magnusson RP, Yu B, Brennan V: Effect of serum thyrotropin levels on the concentration of messenger RNA for thyroid peroxidase in the rat. Acta Endocrinol (Copenh). 1992 May;126(5):460-6. [PubMed:1320313]
- Chiovato L, Pinchera A: The microsomal/peroxidase antigen: modulation of its expression in thyroid cells. Autoimmunity. 1991;10(4):319-31. [PubMed:1663395]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- Curator comments
- Supporting data are limited to in vitro studies.
- General Function
- Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
- Specific Function
- Cytochromes 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 Name
- CYP1A2
- Uniprot ID
- P05177
- Uniprot Name
- Cytochrome P450 1A2
- Molecular Weight
- 58293.76 Da
References
- Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
- Guo Z, Raeissi S, White RB, Stevens JC: Orphenadrine and methimazole inhibit multiple cytochrome P450 enzymes in human liver microsomes. Drug Metab Dispos. 1997 Mar;25(3):390-3. [PubMed:9172960]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Exhibits 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 Name
- CYP2A6
- Uniprot ID
- P11509
- Uniprot Name
- Cytochrome P450 2A6
- Molecular Weight
- 56501.005 Da
References
- Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
- Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [PubMed:11996015]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes 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 Name
- CYP2B6
- Uniprot ID
- P20813
- Uniprot Name
- Cytochrome P450 2B6
- Molecular Weight
- 56277.81 Da
References
- Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
- Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [PubMed:11996015]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- Curator comments
- Current data supporting this enzyme inhibition is limited to one in vitro study.
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible 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 Name
- CYP2C19
- Uniprot ID
- P33261
- Uniprot Name
- Cytochrome P450 2C19
- Molecular Weight
- 55930.545 Da
References
- Guo Z, Raeissi S, White RB, Stevens JC: Orphenadrine and methimazole inhibit multiple cytochrome P450 enzymes in human liver microsomes. Drug Metab Dispos. 1997 Mar;25(3):390-3. [PubMed:9172960]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- Curator comments
- Data supporting this enzyme action are limited to the findings of 1 in vitro study.
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes 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 Name
- CYP2C9
- Uniprot ID
- P11712
- Uniprot Name
- Cytochrome P450 2C9
- Molecular Weight
- 55627.365 Da
References
- Guo Z, Raeissi S, White RB, Stevens JC: Orphenadrine and methimazole inhibit multiple cytochrome P450 enzymes in human liver microsomes. Drug Metab Dispos. 1997 Mar;25(3):390-3. [PubMed:9172960]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible 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 Name
- CYP2D6
- Uniprot ID
- P10635
- Uniprot Name
- Cytochrome P450 2D6
- Molecular Weight
- 55768.94 Da
References
- Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Metabolizes 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 Name
- CYP2E1
- Uniprot ID
- P05181
- Uniprot Name
- Cytochrome P450 2E1
- Molecular Weight
- 56848.42 Da
References
- Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
- Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [PubMed:11996015]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes 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 Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
- Guo Z, Raeissi S, White RB, Stevens JC: Orphenadrine and methimazole inhibit multiple cytochrome P450 enzymes in human liver microsomes. Drug Metab Dispos. 1997 Mar;25(3):390-3. [PubMed:9172960]
Drug created on June 13, 2005 07:24 / Updated on February 18, 2019 20:24