clomifene 🐶 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
  • clomid
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 µM/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
March 11, 2022 PMDA Fuji Pharma Co., Ltd

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 254.23 32.67 110 1644 155437 63331831
Ovarian hyperstimulation syndrome 172.66 32.67 36 1718 3978 63483290
Abortion spontaneous 156.73 32.67 56 1698 47139 63440129
Heterotopic pregnancy 146.93 32.67 16 1738 6 63487262
Multiple pregnancy 93.92 32.67 12 1742 52 63487216
Ectopic pregnancy 93.02 32.67 20 1734 2547 63484721
Gestational diabetes 92.41 32.67 25 1729 8371 63478897
Adnexal torsion 91.38 32.67 15 1739 439 63486829
Retinopathy of prematurity 59.20 32.67 10 1744 349 63486919
Cleft lip 54.07 32.67 8 1746 116 63487152
Twin pregnancy 53.17 32.67 11 1743 1162 63486106
Foetal exposure during pregnancy 53.00 32.67 23 1731 31939 63455329
Pregnancy 49.87 32.67 23 1731 36813 63450455
Maternal exposure before pregnancy 49.30 32.67 15 1739 7588 63479680
Neonatal respiratory distress syndrome 48.57 32.67 12 1742 2806 63484462
Premature baby 48.20 32.67 19 1735 20716 63466552
Abortion threatened 48.14 32.67 9 1745 563 63486705
Maternal exposure during pregnancy 45.63 32.67 42 1712 220020 63267248
Ruptured ectopic pregnancy 43.32 32.67 8 1746 468 63486800
Abortion 39.87 32.67 10 1744 2486 63484782
Caesarean section 37.46 32.67 15 1739 17017 63470251

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 62.07 46.07 23 524 38078 34918306
Testicular atrophy 52.99 46.07 9 538 583 34955801
Muscle mass 52.61 46.07 8 539 256 34956128

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 181.04 30.82 35 1616 3536 79739201
Heterotopic pregnancy 151.55 30.82 16 1635 6 79742731
Exposure during pregnancy 121.15 30.82 53 1598 101079 79641658
Abortion spontaneous 107.66 30.82 35 1616 29472 79713265
Ectopic pregnancy 106.51 30.82 20 1631 1723 79741014
Gestational diabetes 101.49 30.82 24 1627 6269 79736468
Multiple pregnancy 91.94 30.82 11 1640 35 79742702
Adnexal torsion 90.74 30.82 14 1637 369 79742368
Twin pregnancy 65.73 30.82 12 1639 884 79741853
Abortion threatened 53.41 30.82 9 1642 416 79742321
Testicular atrophy 47.62 30.82 8 1643 363 79742374
Maternal exposure before pregnancy 46.78 30.82 12 1639 4361 79738376
Ruptured ectopic pregnancy 46.42 30.82 8 1643 423 79742314
Caesarean section 46.18 30.82 15 1636 12520 79730217
Muscle mass 45.83 30.82 8 1643 456 79742281
Maternal exposure during pregnancy 41.55 30.82 29 1622 136509 79606228
Benign hydatidiform mole 34.27 30.82 5 1646 89 79742648
Pregnancy 31.78 30.82 14 1637 26837 79715900

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
Controlled ovarian stimulation indication 732970000
Induction of spermatogenesis indication
Male infertility off-label use 2904007 DOID:12336
Oligozoospermia off-label use 88311004
Ovarian Function Studies off-label use
Corpus Luteum Insufficiency Syndrome off-label use
Diagonstic Test for Hypothalamic Pituitary Gonadal Axis 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
Visual Disturbance of Seeing Spots contraindication
Scotomata contraindication




🐶 Veterinary Drug Use

None

🐶 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
1548955 PUBCHEM_CID
356 MMSL
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
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 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
CLOMID HUMAN PRESCRIPTION DRUG LABEL 1 50090-6500 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 63629-5302 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