clomifene Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
antiestrogens or estrogen receptor modulators, clomifene and tamoxifen derivatives 700 911-45-5

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • clomifene citrate
  • clomifene
  • clomiphene
  • Clomiphene B
  • clomiphene citrate
A triphenyl ethylene stilbene derivative which is an estrogen agonist or antagonist depending on the target tissue. Note that ENCLOMIPHENE and ZUCLOMIPHENE are the (E) and (Z) isomers of Clomiphene respectively.
  • Molecular weight: 405.97
  • Formula: C26H28ClNO
  • CLOGP: 7.15
  • LIPINSKI: 1
  • HAC: 2
  • HDO: 0
  • TPSA: 12.47
  • ALOGS: -5.99
  • ROTB: 9

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
9 mg O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 1.11 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 8 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 3.52 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 90 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Approvals:

DateAgencyCompanyOrphan
Feb. 1, 1967 FDA SANOFI AVENTIS US

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Ovarian hyperstimulation syndrome 178.51 47.26 35 1133 3157 46681737
Exposure during pregnancy 165.69 47.26 71 1097 108141 46576753
Heterotopic pregnancy 128.10 47.26 14 1154 8 46684886
Multiple pregnancy 102.94 47.26 13 1155 57 46684837
Ectopic pregnancy 89.22 47.26 19 1149 2563 46682331
Abortion spontaneous 84.47 47.26 34 1134 43612 46641282
Adnexal torsion 78.59 47.26 12 1156 242 46684652
Twin pregnancy 66.23 47.26 13 1155 1168 46683726
Retinopathy of prematurity 62.69 47.26 10 1158 270 46684624
Maternal exposure during pregnancy 59.48 47.26 35 1133 102514 46582380
Neonatal respiratory distress syndrome 51.05 47.26 12 1156 2521 46682373
Premature baby 48.86 47.26 18 1150 18094 46666800
Abortion threatened 48.62 47.26 9 1159 591 46684303

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event

Pharmacologic Action:

SourceCodeDescription
ATC G03GB02 GENITO URINARY SYSTEM AND SEX HORMONES
SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
GONADOTROPINS AND OTHER OVULATION STIMULANTS
Ovulation stimulants, synthetic
FDA MoA N0000000168 Selective Estrogen Receptor Modulators
FDA EPC N0000175826 Estrogen Agonist/Antagonist
CHEBI has role CHEBI:50837 oestrogen antagonist
CHEBI has role CHEBI:50751 anti-estrogenic agent
MeSH PA D004965 Estrogen Antagonists
MeSH PA D020847 Estrogen Receptor Modulators
MeSH PA D005300 Fertility Agents, Female
MeSH PA D006727 Hormone Antagonists
MeSH PA D012102 Reproductive Control Agents
MeSH PA D020845 Selective Estrogen Receptor Modulators

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Female infertility indication 6738008
Ovulation induction indication 61285001
Male infertility off-label use 2904007 DOID:12336
Oligozoospermia off-label use 88311004
Diagonstic Test for Hypothalamic Pituitary Gonadal Axis off-label use
Corpus Luteum Insufficiency Syndrome off-label use
Ovarian Function Studies off-label use
Severe adrenal insufficiency contraindication 24867002
Depressive disorder contraindication 35489007
Hypothyroidism contraindication 40930008 DOID:1459
Thrombophlebitis contraindication 64156001 DOID:3875
Intermenstrual bleeding - irregular contraindication 64996003
Polycystic ovaries contraindication 69878008
Cyst of ovary contraindication 79883001
Thyrotoxicosis contraindication 90739004 DOID:7997
Neoplasm of pituitary gland contraindication 127024001 DOID:1785
Endometriosis contraindication 129103003
Ovarian hyperstimulation syndrome contraindication 129635004 DOID:5425
Disease of liver contraindication 235856003 DOID:409
Endometrial carcinoma contraindication 254878006 DOID:2871
Pregnancy, function contraindication 289908002
Lesion of brain contraindication 301766008
Thromboembolic disorder contraindication 371039008
Visual impairment contraindication 397540003
Scotomata contraindication
Visual Disturbance of Seeing Spots contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 8.9 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Estrogen receptor Nuclear hormone receptor MODULATOR Ki 8.89 DRUG MATRIX CHEMBL
Alpha-2A adrenergic receptor GPCR Ki 6.45 DRUG MATRIX
Sodium-dependent serotonin transporter Transporter Ki 6.47 DRUG MATRIX
Sodium-dependent noradrenaline transporter Transporter Ki 6.07 DRUG MATRIX
5-hydroxytryptamine receptor 2A GPCR Ki 6.02 DRUG MATRIX
5-hydroxytryptamine receptor 2B GPCR Ki 6.06 DRUG MATRIX
5-hydroxytryptamine receptor 2C GPCR Ki 6.18 DRUG MATRIX
Alpha-2B adrenergic receptor GPCR Ki 6.14 DRUG MATRIX
D(3) dopamine receptor GPCR Ki 6.35 DRUG MATRIX
Muscarinic acetylcholine receptor M1 GPCR Ki 6.41 DRUG MATRIX
Muscarinic acetylcholine receptor M2 GPCR Ki 5.89 DRUG MATRIX
Muscarinic acetylcholine receptor M3 GPCR Ki 6.36 DRUG MATRIX
Muscarinic acetylcholine receptor M4 GPCR Ki 6.64 DRUG MATRIX
Muscarinic acetylcholine receptor M5 GPCR Ki 5.90 DRUG MATRIX
Beta-3 adrenergic receptor GPCR Ki 5.37 DRUG MATRIX
Alpha-2C adrenergic receptor GPCR Ki 6.67 DRUG MATRIX
Sodium-dependent dopamine transporter Transporter Ki 6.21 DRUG MATRIX
Cytochrome P450 2D6 Enzyme IC50 5 DRUG MATRIX
Adenosine receptor A3 GPCR Ki 5.52 DRUG MATRIX
Epidermal growth factor receptor Kinase IC50 5.98 DRUG MATRIX
Tyrosine-protein kinase Fyn Kinase IC50 5.60 DRUG MATRIX
Receptor tyrosine-protein kinase erbB-2 Kinase IC50 5.78 DRUG MATRIX
Substance-K receptor GPCR Ki 5.82 DRUG MATRIX
Potassium voltage-gated channel subfamily H member 2 Ion channel IC50 6.74 WOMBAT-PK
Histamine H1 receptor GPCR Ki 5.19 WOMBAT-PK
Sigma non-opioid intracellular receptor 1 Membrane receptor Ki 8.10 CHEMBL
5-hydroxytryptamine receptor 6 GPCR Ki 5.71 CHEMBL
Prostaglandin G/H synthase 1 Enzyme IC50 6.46 DRUG MATRIX
3-beta-hydroxysteroid-Delta(8),Delta(7)-isomerase Enzyme Ki 9 CHEMBL
Alpha-1B adrenergic receptor GPCR Ki 5.60 DRUG MATRIX
Membrane-associated progesterone receptor component 1 Membrane receptor Ki 7.52 DRUG MATRIX
C-8 sterol isomerase Enzyme Ki 6.80 CHEMBL
Androgen receptor Transcription factor IC50 4.87 CHEMBL

External reference:

IDSource
4018616 VUID
N0000179535 NUI
D00962 KEGG_DRUG
50-41-9 SECONDARY_CAS_RN
4018616 VANDF
4019686 VANDF
C0009008 UMLSCUI
CHEBI:3752 CHEBI
53Q PDB_CHEM_ID
CHEMBL2355051 ChEMBL_ID
CHEMBL3185958 ChEMBL_ID
DB00882 DRUGBANK_ID
D002996 MESH_DESCRIPTOR_UI
2800 PUBCHEM_CID
4159 IUPHAR_LIGAND_ID
1309 INN_ID
1HRS458QU2 UNII
142431 RXNORM
362 MMSL
4475 MMSL
d00569 MMSL
002101 NDDF
004781 NDDF
30466001 SNOMEDCT_US
387166005 SNOMEDCT_US
387346007 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Clomiphene Citrate HUMAN PRESCRIPTION DRUG LABEL 1 21695-114 TABLET 50 mg ORAL ANDA 18 sections
Clomiphene Citrate HUMAN PRESCRIPTION DRUG LABEL 1 49884-701 TABLET 50 mg ORAL ANDA 17 sections
Clomiphene Citrate HUMAN PRESCRIPTION DRUG LABEL 1 50090-0677 TABLET 50 mg ORAL NDA authorized generic 22 sections
Clomiphene Citrate HUMAN PRESCRIPTION DRUG LABEL 1 50090-0678 TABLET 50 mg ORAL ANDA 17 sections
Clomiphene Citrate HUMAN PRESCRIPTION DRUG LABEL 1 54868-3059 TABLET 50 mg ORAL ANDA 17 sections
CLOMIPHENE CITRATE HUMAN PRESCRIPTION DRUG LABEL 1 61919-375 TABLET 50 mg ORAL ANDA 10 sections
Clomiphene Citrate HUMAN PRESCRIPTION DRUG LABEL 1 63629-2165 TABLET 50 mg ORAL ANDA 17 sections
Clomiphene Citrate HUMAN PRESCRIPTION DRUG LABEL 1 63629-5302 TABLET 50 mg ORAL ANDA 17 sections
Clomiphene Citrate HUMAN PRESCRIPTION DRUG LABEL 1 68071-4676 TABLET 50 mg ORAL ANDA 17 sections