toremifene 🐶 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	2709	89778-26-7

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: FC1157a FC-1157a FC 1157a fareston toremifene chlortamoxifen toremifene citrate	A first generation selective estrogen receptor modulator (SERM). Like TAMOXIFEN, it is an estrogen agonist for bone tissue and cholesterol metabolism but is antagonistic on mammary and uterine tissue. Molecular weight: 405.97 Formula: C26H28ClNO CLOGP: 6.53 LIPINSKI: 1 HAC: 2 HDO: 0 TPSA: 12.47 ALOGS: -6 ROTB: 9 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

FC1157a
FC-1157a
FC 1157a
fareston
toremifene
chlortamoxifen
toremifene citrate

A first generation selective estrogen receptor modulator (SERM). Like TAMOXIFEN, it is an estrogen agonist for bone tissue and cholesterol metabolism but is antagonistic on mammary and uterine tissue.

Molecular weight: 405.97
Formula: C26H28ClNO
CLOGP: 6.53
LIPINSKI: 1
HAC: 2
HDO: 0
TPSA: 12.47
ALOGS: -6
ROTB: 9

Status: OFP

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

Drug dosage:

Dose	Unit	Route
60	mg	O

ADMET properties:

Property	Value	Reference
BDDCS (Biopharmaceutical Drug Disposition Classification System)	1	Benet LZ, Broccatelli F, Oprea TI
S (Water solubility)	0.38 mg/mL	Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine)	0.10 %	Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose)	8.20 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability)	99 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Approvals:

Date	Agency	Company	Orphan
May 29, 1997	FDA	PROSTRAKAN INC

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
Osteonecrosis of jaw	76.60	38.41	24	654	35099	63453245
Osteomyelitis	49.31	38.41	16	662	26004	63462340

FDA Adverse Event Reporting System (Male)

None

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
Osteonecrosis of jaw	61.12	36.33	19	515	43207	79700647
Osteomyelitis	40.40	36.33	13	521	32852	79711002
General physical health deterioration	39.91	36.33	24	510	275214	79468640
Pseudocirrhosis	37.14	36.33	6	528	674	79743180

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

Source	Code	Description
ATC	L02BA02	ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS ENDOCRINE THERAPY HORMONE ANTAGONISTS AND RELATED AGENTS Anti-estrogens
FDA MoA	N0000000168	Selective Estrogen Receptor Modulators
CHEBI has role	CHEBI:35610	antineoplastic agents
CHEBI has role	CHEBI:50646	antiosteoporotic
CHEBI has role	CHEBI:50837	oestrogen antagonist
CHEBI has role	CHEBI:149553	anticoronaviral drug
FDA EPC	N0000175826	Estrogen Agonist/Antagonist
MeSH PA	D000970	Antineoplastic Agents
MeSH PA	D018931	Antineoplastic Agents, Hormonal
MeSH PA	D050071	Bone Density Conservation Agents
MeSH PA	D020847	Estrogen Receptor Modulators
MeSH PA	D006727	Hormone Antagonists
MeSH PA	D020845	Selective Estrogen Receptor Modulators

Drug Use | Suggest Off label Use Form| |View source of the data|

Disease	Relation	SNOMED_ID	DOID
Metastatic Breast Carcinoma	indication
Torsades de pointes	contraindication	31722008
Hypokalemia	contraindication	43339004
Hypercalcemia	contraindication	66931009	DOID:12678
Leukopenia	contraindication	84828003	DOID:615
Prolonged QT interval	contraindication	111975006
Hypomagnesemia	contraindication	190855004
Endometrial hyperplasia	contraindication	237072009
Pregnancy, function	contraindication	289908002
Thrombocytopenic disorder	contraindication	302215000	DOID:1588
Thromboembolic disorder	contraindication	371039008
Breastfeeding (mother)	contraindication	413712001
Congenital long QT syndrome	contraindication	442917000

🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	8.61	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])	Bioact source	MoA source
Estrogen receptor	Nuclear hormone receptor	P03372	ESR1_HUMAN	MODULATOR			WOMBAT-PK	CHEMBL
5-hydroxytryptamine receptor 6	GPCR	P50406	5HT6R_HUMAN		Ki	5.38	CHEMBL
Estrogen-related receptor gamma	Nuclear hormone receptor	P62508	ERR3_HUMAN				WOMBAT-PK
Envelope glycoprotein	Unclassified		VGP_EBOZM		Kd	4.80	CHEMBL

External reference:

ID	Source
D00967	KEGG_DRUG
89778-27-8	SECONDARY_CAS_RN
4021088	VANDF
4024102	VANDF
C0076836	UMLSCUI
CHEBI:9635	CHEBI
T0R	PDB_CHEM_ID
CHEMBL1655	ChEMBL_ID
CHEMBL1200675	ChEMBL_ID
D017312	MESH_DESCRIPTOR_UI
DB00539	DRUGBANK_ID
3005573	PUBCHEM_CID
4325	IUPHAR_LIGAND_ID
5698	INN_ID
7NFE54O27T	UNII
155082	RXNORM
11447	MMSL
305699	MMSL
5603	MMSL
d04137	MMSL
006098	NDDF
007222	NDDF
387057008	SNOMEDCT_US
387588002	SNOMEDCT_US
96378009	SNOMEDCT_US

Pharmaceutical products:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Fareston	HUMAN PRESCRIPTION DRUG LABEL	1	42747-327	TABLET	60 mg	ORAL	NDA	27 sections
Fareston	HUMAN PRESCRIPTION DRUG LABEL	1	42747-327	TABLET	60 mg	ORAL	NDA	27 sections
Toremifene Citrate	Human Prescription Drug Label	1	64980-404	TABLET	60 mg	ORAL	ANDA	28 sections
toremifene citrate	Human Prescription Drug Label	1	69539-152	TABLET	60 mg	ORAL	ANDA	26 sections
toremifene citrate	Human Prescription Drug Label	1	72205-050	TABLET	60 mg	ORAL	ANDA	26 sections