clomifene ๐Ÿถ Veterinary Use | 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 ยตM/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
Exposure during pregnancy 258.56 47.13 104 1321 120911 50482788
Ovarian hyperstimulation syndrome 179.71 47.13 36 1389 3208 50600491
Abortion spontaneous 162.57 47.13 56 1369 41716 50561983
Heterotopic pregnancy 148.98 47.13 16 1409 3 50603696
Multiple pregnancy 94.88 47.13 12 1413 46 50603653
Ectopic pregnancy 88.92 47.13 19 1406 2308 50601391
Adnexal torsion 70.26 47.13 11 1414 232 50603467
Gestational diabetes 66.91 47.13 19 1406 7446 50596253
Retinopathy of prematurity 59.65 47.13 10 1415 327 50603372
Foetal exposure during pregnancy 56.06 47.13 23 1402 27336 50576363
Cleft lip 54.66 47.13 8 1417 105 50603594
Twin pregnancy 53.54 47.13 11 1414 1102 50602597
Maternal exposure during pregnancy 52.35 47.13 40 1385 159738 50443961
Pregnancy 51.02 47.13 22 1403 29555 50574144
Premature baby 50.14 47.13 19 1406 18318 50585381
Neonatal respiratory distress syndrome 49.07 47.13 12 1413 2642 50601057
Maternal exposure before pregnancy 49.04 47.13 14 1411 5583 50598116
Abortion threatened 48.44 47.13 9 1416 534 50603165

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
Foetal exposure during pregnancy 64.25 47.96 23 451 33844 29540209

FDA Adverse Event Reporting System (Geriatric)

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 191.08 38.24 35 1227 2810 64494660
Heterotopic pregnancy 154.82 38.24 16 1246 3 64497467
Exposure during pregnancy 120.11 38.24 48 1214 77627 64419843
Abortion spontaneous 115.23 38.24 35 1227 25108 64472362
Ectopic pregnancy 103.37 38.24 19 1243 1545 64495925
Multiple pregnancy 93.31 38.24 11 1251 32 64497438
Gestational diabetes 74.10 38.24 18 1244 5572 64491898
Adnexal torsion 68.76 38.24 10 1252 185 64497285
Twin pregnancy 67.09 38.24 12 1250 835 64496635
Abortion threatened 54.18 38.24 9 1253 404 64497066
Caesarean section 48.60 38.24 15 1247 11259 64486211
Ruptured ectopic pregnancy 47.80 38.24 8 1254 376 64497094
Maternal exposure during pregnancy 47.13 38.24 27 1235 95857 64401613
Maternal exposure before pregnancy 45.04 38.24 11 1251 3472 64493998
Testicular atrophy 41.70 38.24 7 1255 335 64497135
Muscle mass 40.38 38.24 7 1255 406 64497064

FDA Adverse Event Reporting System (Pediatric)

None

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
CHEBI has role CHEBI:50837 oestrogen antagonist
CHEBI has role CHEBI:50751 anti-estrogenic drug
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
FDA EPC N0000175826 Estrogen Agonist/Antagonist

Drug Use | Suggest Off label Use Form| |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




๐Ÿถ Veterinary Drug Use

None

๐Ÿถ Veterinary products

None

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 6.46 DRUG MATRIX
Sigma non-opioid intracellular receptor 1 Membrane receptor Ki 8.10 CHEMBL
Potassium voltage-gated channel subfamily H member 2 Ion channel IC50 6.75 WOMBAT-PK
3-beta-hydroxysteroid-Delta(8),Delta(7)-isomerase Enzyme Ki 9 CHEMBL
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 6.03 DRUG MATRIX
5-hydroxytryptamine receptor 2B GPCR Ki 6.06 DRUG MATRIX
5-hydroxytryptamine receptor 2C GPCR Ki 6.18 DRUG MATRIX
5-hydroxytryptamine receptor 6 GPCR Ki 5.71 CHEMBL
Alpha-2B adrenergic receptor GPCR Ki 6.14 DRUG MATRIX
D(3) dopamine receptor GPCR Ki 6.35 DRUG MATRIX
Histamine H1 receptor GPCR Ki 5.19 WOMBAT-PK
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
Prostaglandin G/H synthase 1 Enzyme IC50 6.46 DRUG MATRIX
Androgen receptor Transcription factor IC50 4.87 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

External reference:

IDSource
4018616 VUID
N0000179535 NUI
D00962 KEGG_DRUG
50-41-9 SECONDARY_CAS_RN
142431 RXNORM
4018616 VANDF
4019686 VANDF
C0009008 UMLSCUI
CHEBI:3752 CHEBI
53Q PDB_CHEM_ID
CHEMBL2355051 ChEMBL_ID
CHEMBL3185958 ChEMBL_ID
DB00882 DRUGBANK_ID
4159 IUPHAR_LIGAND_ID
1548953 PUBCHEM_CID
362 MMSL
4475 MMSL
d00569 MMSL
002101 NDDF
004781 NDDF
30466001 SNOMEDCT_US
387166005 SNOMEDCT_US
387346007 SNOMEDCT_US
D002996 MESH_DESCRIPTOR_UI
1309 INN_ID
1HRS458QU2 UNII

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Clomid HUMAN PRESCRIPTION DRUG LABEL 1 0713-0885 TABLET 50 mg ORAL ANDA 17 sections
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 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 63629-2165 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 63629-5302 TABLET 50 mg ORAL ANDA 17 sections
Clomiphene Citrate HUMAN PRESCRIPTION DRUG LABEL 1 63629-9276 TABLET 50 mg ORAL ANDA 17 sections
Clomiphene Citrate HUMAN PRESCRIPTION DRUG LABEL 1 68071-2638 TABLET 50 mg ORAL ANDA 17 sections
Clomiphene Citrate HUMAN PRESCRIPTION DRUG LABEL 1 68071-4676 TABLET 50 mg ORAL ANDA 17 sections