phenprocoumon 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
anticoagulants, dicoumarol derivatives	2138	435-97-2

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: phenprocoumon fencumar marcoumar phenprocoumarol phenprocoumarole liquamar	Coumarin derivative that acts as a long acting oral anticoagulant. Molecular weight: 280.32 Formula: C18H16O3 CLOGP: 4.71 LIPINSKI: 0 HAC: 3 HDO: 1 TPSA: 46.53 ALOGS: -3.76 ROTB: 3 Status: OFM Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

phenprocoumon
fencumar
marcoumar
phenprocoumarol
phenprocoumarole
liquamar

Coumarin derivative that acts as a long acting oral anticoagulant.

Molecular weight: 280.32
Formula: C18H16O3
CLOGP: 4.71
LIPINSKI: 0
HAC: 3
HDO: 1
TPSA: 46.53
ALOGS: -3.76
ROTB: 3

Status: OFM

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

Drug dosage:

Dose	Unit	Route
3	mg	O

ADMET properties:

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Property	Value	Reference
t_half (Half-life)	126 hours	Lombardo F, Berellini G, Obach RS
MRTD (Maximum Recommended Therapeutic Daily Dose)	1.43 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BDDCS (Biopharmaceutical Drug Disposition Classification System)	1	Bocci G, Oprea TI, Benet LZ
fu (Fraction unbound in plasma)	0.57 %	Lombardo F, Berellini G, Obach RS
Vd (Volume of distribution)	0.20 L/kg	Lombardo F, Berellini G, Obach RS
CL (Clearance)	0.02 mL/min/kg	Lombardo F, Berellini G, Obach RS
S (Water solubility)	0.01 mg/mL	Bocci G, Oprea TI, Benet LZ

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Approvals:

Date	Agency	Company	Orphan
Dec. 30, 1957	FDA	ORGANON USA INC

FDA Adverse Event Reporting System (Female)

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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
General physical health deterioration	282.35	26.97	205	6534	201197	63281086
Product monitoring error	250.01	26.97	64	6675	4452	63477831
Product prescribing error	240.02	26.97	94	6645	26195	63456088
Haematochezia	127.13	26.97	76	6663	53468	63428815
Anaemia	121.19	26.97	152	6587	293278	63189005
Haematoma	119.62	26.97	63	6676	34757	63447526
Acute kidney injury	112.80	26.97	139	6600	263276	63219007
Atrial fibrillation	101.36	26.97	90	6649	116546	63365737
Labelled drug-drug interaction medication error	98.35	26.97	41	6698	13358	63468925
Cardiac failure	87.98	26.97	74	6665	89068	63393215

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FDA Adverse Event Reporting System (Male)

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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
Product prescribing error	197.48	21.16	105	9475	22822	34924529
General physical health deterioration	158.56	21.16	185	9395	128084	34819267
Product monitoring error	149.08	21.16	53	9527	4328	34943023
International normalised ratio abnormal	127.47	21.16	44	9536	3291	34944060
Contraindicated product administered	92.39	21.16	63	9517	21418	34925933
Rectal prolapse	90.24	21.16	22	9558	470	34946881
Renal cyst haemorrhage	84.53	21.16	22	9558	617	34946734
Intestinal haemorrhage	81.28	21.16	32	9548	3464	34943887
Intraductal papillary mucinous neoplasm	78.48	21.16	20	9560	515	34946836
Haematoma	69.55	21.16	57	9523	25548	34921803

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FDA Adverse Event Reporting System (Geriatric)

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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
Product prescribing error	434.87	20.75	198	14941	44615	79684634
General physical health deterioration	405.92	20.75	368	14771	274870	79454379
Product monitoring error	372.39	20.75	115	15024	8791	79720458
Haematochezia	171.07	20.75	138	15001	87507	79641742
Haematoma	157.82	20.75	107	15032	52088	79677161
International normalised ratio abnormal	142.24	20.75	50	15089	5718	79723531
International normalised ratio increased	133.59	20.75	118	15021	84603	79644646
Anaemia	123.51	20.75	265	14874	444750	79284499
Drug ineffective	95.88	20.75	43	15096	1080870	78648379
Labelled drug-drug interaction medication error	93.97	20.75	61	15078	27589	79701660

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	B01AA04	BLOOD AND BLOOD FORMING ORGANS ANTITHROMBOTIC AGENTS ANTITHROMBOTIC AGENTS Vitamin K antagonists
CHEBI has role	CHEBI:50249	anticoagulants
CHEBI has role	CHEBI:50390	NAD(P)H dehydrogenase (quinone) inhibitors
FDA EPC	N0000175476	Vitamin K Antagonist
FDA MoA	N0000175964	Vitamin K Inhibitors
MeSH PA	D000925	Anticoagulants
MeSH PA	D006401	Hematologic Agents

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

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Disease	Relation	SNOMED_ID	DOID
Myocardial infarction	indication	22298006	DOID:5844
Thromboembolic disorder	indication	371039008
Thrombosis	indication	439127006
Prosthetic replacement of heart valve	off-label use	307279007

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🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	4.51	acidic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

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Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
Vitamin K epoxide reductase complex subunit 1	Enzyme	Q9BQB6	VKOR1_HUMAN	INHIBITOR	IC50	5.75	SCIENTIFIC LITERATURE	CHEMBL
Pol polyprotein	Enzyme		Q72874_9HIV1		Ki	6.10	CHEMBL
Vitamin K epoxide reductase complex subunit 1	Unclassified		VKOR1_RAT		Ki	6.70	CHEMBL

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External reference:

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ID	Source
002086	NDDF
247	INN_ID
4018525	VUID
4018525	VANDF
54680692	PUBCHEM_CID
59488002	SNOMEDCT_US
6839	IUPHAR_LIGAND_ID
8150	RXNORM
C0031444	UMLSCUI
CHEBI:50438	CHEBI

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Pharmaceutical products:

None