Details of the Drug

General Information of Drug (ID: DMKI7RB)

Drug Name
Clomifene
Synonyms
Androxal; Chlomaphene; Chloramifene; Cisclomifenum; Cisclomiphene; Clomifen; Clomifeno; Clomifenum; Clomifert; Clomiphene; Clostilbegit; Enclomifene; Enclomifeno; Enclomifenum; Enclomiphen; Enclomiphene; Klostilbegit; Transclomifenum; Transclomiphene; Zuclomifene; Zuclomifeno; Zuclomifenum; Zuclomiphene; Clomiphene B;Enclomiphene [USAN]; ISOMER B; Zuclomiphene [USAN]; Cis-Clomifene; Cis-Clomiphene; Clomid (TN); Clomifene (INN); Clomifene (TN); Clomifene [INN:BAN]; Clomifeno [INN-Spanish]; Clomifenum [INN-Latin]; En-Clomiphene; Enclomifeno [INN-Spanish]; Enclomifenum [INN-Latin]; Enclomiphene (USAN); Milophene (TN); RMI 16,289; RMI-16289; RMI-16312; Serophene (TN); Trans-Clomifene; Trans-Clomiphene; Zuclomifeno [INN-Spanish]; Zuclomifenum [INN-Latin]; Zuclomiphene (USAN); Cis-2-(p-(2-Chloro-1,2-diphenylvinyl)phenoxy)triethylamine; Trans-2-(p-(2-Chloro-1,2-diphenylvinyl)phenoxy)triethylamine; Cis-2-(4-(2-Chloro-1,2-diphenylethenyl)phenoxy)-N,N-diethylethanamine; Trans-2-(4-(2-Chloro-1,2-diphenylethenyl)phenoxy)-N,N-diethylethanamine; (E)-2-(p-(2-Chloro-1,2-diphenylvinyl)phenoxy)triethylamine; (Z)-2-(p-(2-Chloro-1,2-diphenylvinyl)phenoxy)triethylamine; (Z)-isomer; 1-(p-(beta-Diethylaminoethoxy)-phenyl)-1,2-diphenylchloroethylene; 2-(4-(2-Chloro-1,2-diphenylethenyl)phenoxy)-N,N-diethylethanamine; 2-(p-(2-Chloro-1,2-diphenylvinyl)phenoxy)triethylamine; 2-(p-(beta-Chloro-alpha-phenylstyryl)phenoxy)-triethylamine; 2-(p-(beta-chloro-alpha-phenylstyryl)phenoxy)triethylamine; 2-({4-[(Z)-2-chloro-1,2-diphenylethenyl]phenyl}oxy)-N,N-diethylethanamine; 2-[4-(2-chloro-1,2-diphenylethenyl)phenoxy]-N,N-diethylethanamine; 2-[4-[(E)-2-chloro-1,2-diphenylethenyl]phenoxy]-N,N-diethylethanamine; 2-[4-[(Z)-2-chloro-1,2-diphenylethenyl]phenoxy]-N,N-diethylethanamine; 2-{4-[(E)-2-chloro-1,2-diphenylethenyl]phenoxy}-N,N-diethylethanamine
Indication
Disease Entry ICD 11 Status REF
Female infertility GA31.Z Approved [1]
Hypogonadotropic hypogonadism N.A. Approved [2]
Therapeutic Class
Fertility Agents
ATC Code
G03GB02: Clomifene
G03GB: Ovulation stimulants, synthetic
G03G: GONADOTROPINS AND OTHER OVULATION STIMULANTS
G03: SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
G: GENITO URINARY SYSTEM AND SEX HORMONES
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 406
Logarithm of the Partition Coefficient (xlogp) 7.2
Rotatable Bond Count (rotbonds) 9
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 2
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability [3]
Bioavailability
90% of drug becomes completely available to its intended biological destination(s) [4]
Elimination
8% of drug is excreted from urine in the unchanged form [3]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 3.519 micromolar/kg/day [5]
Water Solubility
The ability of drug to dissolve in water is measured as 1.11 mg/mL [3]
Chemical Identifiers
Formula
C26H28ClNO
IUPAC Name
2-[4-[(E)-2-chloro-1,2-diphenylethenyl]phenoxy]-N,N-diethylethanamine
Canonical SMILES
CCN(CC)CCOC1=CC=C(C=C1)/C(=C(\\C2=CC=CC=C2)/Cl)/C3=CC=CC=C3
InChI
InChI=1S/C26H28ClNO/c1-3-28(4-2)19-20-29-24-17-15-22(16-18-24)25(21-11-7-5-8-12-21)26(27)23-13-9-6-10-14-23/h5-18H,3-4,19-20H2,1-2H3/b26-25+
InChIKey
GKIRPKYJQBWNGO-OCEACIFDSA-N
Cross-matching ID
PubChem CID
1548953
ChEBI ID
CHEMBL954
CAS Number
15690-57-0
UNII
R6D2UI4FLS
DrugBank ID
DB06735
TTD ID
D0CT9Y
VARIDT ID
DR01391
INTEDE ID
DR0577
ACDINA ID
D00138
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug Pharmacogenomic Perturbation (DPP)NEW Click to Jump to the Detailed DPP Information of This Drug
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Estrogen receptor (ESR) TTZAYWL ESR1_HUMAN Modulator [6]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
P-glycoprotein 1 (ABCB1) DTUGYRD MDR1_HUMAN Substrate [7]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 2D6 (CYP2D6)
Main DME 		DECB0K3 CP2D6_HUMAN Substrate [8]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Female infertility
ICD Disease Classification GA31.Z
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
P-glycoprotein 1 (ABCB1) DTP P-GP 7.23E-01 -8.20E-02 -3.22E-01
Cytochrome P450 2D6 (CYP2D6) DME CYP2D6 7.95E-01 -7.47E-02 -2.45E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG
DIG Name DIG ID PubChem CID Functional Classification
Beta-D-lactose E00099 6134 Diluent; Dry powder inhaler carrier; Lyophilization aid
Lactose monohydrate E00393 104938 Binding agent; Diluent; Dry powder inhaler carrier; Lyophilization aid
Magnesium stearate E00208 11177 lubricant
Saccharose E00091 5988 Binding agent; Coating agent; Cryoprotectant; Diluent; Flavoring agent; Suspending agent; Viscosity-controlling agent
Silicon dioxide E00670 Not Available Anticaking agent; Opacifying agent; Viscosity-controlling agent
Pharmaceutical Formulation
Formulation Name Drug Dosage Dosage Form Route
Clomifene 50 mg tablet 50 mg Oral Tablet Oral
Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7619).
2 [Stimulation of spermatogenesis: For whom? Why? How?]. Gynecol Obstet Fertil. 2016 Sep;44(9):505-16.
3 BDDCS applied to over 900 drugs
4 Critical Evaluation of Human Oral Bioavailability for Pharmaceutical Drugs by Using Various Cheminformatics Approaches
5 Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
6 The future of the new selective estrogen receptor modulators. Menopause Int. 2007 Mar;13(1):27-34.
7 Antiestrogens and steroid hormones: substrates of the human P-glycoprotein. Biochem Pharmacol. 1994 Jul 19;48(2):287-92.
8 CYP2D6 is primarily responsible for the metabolism of clomiphene. Drug Metab Pharmacokinet. 2008;23(2):101-5.