clomifene 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |
| Stem definition | Drug id | CAS RN |
|---|---|---|
| antiestrogens or estrogen receptor modulators, clomifene and tamoxifen derivatives | 700 | 911-45-5 |
Description:
| Molecule | Description |
|---|---|
|
Synonyms:
|
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.
Legend: OFP - off patent OFM - off market ONP - on patent |
Drug dosage:
| Dose | Unit | Route |
|---|---|---|
| 9 | mg | O |
ADMET properties:
| Property | Value | Reference |
|---|---|---|
| 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:
| Date | Agency | Company | Orphan |
|---|---|---|---|
| Feb. 1, 1967 | FDA | SANOFI AVENTIS US |
FDA Adverse Event Reporting System (Female)
| MedDRA adverse event term | Likelihood ratio | Likelihood ratio threshold | Patients taking drug having adverse event | Patients taking drug not having adverse event | Patients not taking drug having adverse event | Patients 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 term | Likelihood ratio | Likelihood ratio threshold | Patients taking drug having adverse event | Patients taking drug not having adverse event | Patients not taking drug having adverse event | Patients 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 term | Likelihood ratio | Likelihood ratio threshold | Patients taking drug having adverse event | Patients taking drug not having adverse event | Patients not taking drug having adverse event | Patients 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:
| Source | Code | Description |
|---|---|---|
| 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|
| Disease | Relation | SNOMED_ID | DOID |
|---|---|---|---|
| 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 |
🐶 Veterinary Drug Use
None
🐶 Veterinary products
None
Acid dissociation constants calculated using MoKa v3.0.0
| Dissociation level | Dissociation constant | Type (acidic/basic) |
|---|---|---|
| pKa1 | 8.9 | Basic |
Orange Book patent data (new drug applications)
None
Orange Book exclusivity data (new drug applications)
None
Bioactivity Summary:
| Target | Class | Pharos | UniProt | Action | Type | Activity value (-log[M]) | Mechanism action | Bioact source | MoA 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:
| ID | Source |
|---|---|
| 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:
| Product | Category | Ingredients | NDC | Form | Quantity | Route | Marketing | Label |
|---|---|---|---|---|---|---|---|---|
| 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 |