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:

Property	Value	Reference
MRTD (Maximum Recommended Therapeutic Daily Dose)	1.43 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
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
fu (Fraction unbound in plasma)	0.57 %	Lombardo F, Berellini G, Obach RS
t_half (Half-life)	126 hours	Lombardo F, Berellini G, Obach RS

Approvals:

Date	Agency	Company	Orphan
Dec. 30, 1957	FDA	ORGANON USA 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
General physical health deterioration	257.41	25.10	173	5499	142261	50457191
Product prescribing error	198.06	25.10	78	5594	20883	50578569
Product monitoring error	159.76	25.10	41	5631	2723	50596729
Atrial fibrillation	99.65	25.10	86	5586	101659	50497793
Haematochezia	92.82	25.10	57	5615	39825	50559627
Anaemia	86.84	25.10	123	5549	252333	50347119
Haematoma	79.76	25.10	47	5625	30463	50568989
Cardiac failure	75.86	25.10	65	5607	75975	50523477
Drug interaction	75.68	25.10	102	5570	199519	50399933
International normalised ratio increased	71.81	25.10	50	5622	43102	50556350
Labelled drug-drug interaction medication error	65.24	25.10	29	5643	10448	50589004
Fall	62.37	25.10	124	5548	334808	50264644
Bradycardia	60.05	25.10	53	5619	64373	50535079
Acute kidney injury	57.04	25.10	96	5576	227962	50371490
Drug ineffective	55.98	25.10	12	5660	819321	49780131
Device stimulation issue	54.68	25.10	9	5663	59	50599393
Arrhythmia	51.87	25.10	37	5635	33095	50566357
Pallor	51.00	25.10	32	5640	23167	50576285
Painful respiration	41.76	25.10	14	5658	2361	50597091
Foetal chromosome abnormality	39.56	25.10	6	5666	21	50599431
Therapeutic drug monitoring analysis not performed	38.49	25.10	10	5662	695	50598757
Prothrombin time prolonged	38.14	25.10	19	5653	8819	50590633
Electrocardiogram abnormal	37.78	25.10	18	5654	7587	50591865
Syncope	36.45	25.10	51	5621	102951	50496501
Eosinophilic granulomatosis with polyangiitis	36.27	25.10	12	5660	1943	50597509
Gastrointestinal haemorrhage	33.21	25.10	41	5631	73280	50526172
Vitamin K deficiency	33.08	25.10	8	5664	415	50599037
Cerebral haemorrhage	32.95	25.10	26	5646	27026	50572426
Urogenital haemorrhage	31.85	25.10	7	5665	237	50599215
Dyspnoea	31.69	25.10	133	5539	547475	50051977
Dehydration	31.36	25.10	59	5613	152390	50447062
Pulmonary vein occlusion	31.09	25.10	6	5666	105	50599347
Dizziness	30.95	25.10	97	5575	346272	50253180
Systemic infection	30.64	25.10	11	5661	2272	50597180
Tachycardia	30.35	25.10	46	5626	99717	50499735
Angina pectoris	29.41	25.10	24	5648	26164	50573288
Fracture	29.13	25.10	20	5652	16813	50582639
International normalised ratio decreased	27.49	25.10	12	5660	4136	50595316
Dysmorphism	27.43	25.10	10	5662	2157	50597295
Skin haemorrhage	27.30	25.10	14	5658	6904	50592548
Faecaloma	26.94	25.10	14	5658	7094	50592358
Hygroma colli	26.60	25.10	4	5668	13	50599439
Epistaxis	26.16	25.10	34	5638	63920	50535532
Dandy-Walker syndrome	25.62	25.10	5	5667	93	50599359
Blood loss anaemia	25.16	25.10	14	5658	8125	50591327

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
General physical health deterioration	155.48	21.12	164	7862	102693	29463808
Product prescribing error	154.65	21.12	82	7944	17894	29548607
Contraindicated product administered	89.79	21.12	58	7968	18208	29548293
International normalised ratio abnormal	75.83	21.12	29	7997	2934	29563567
Intestinal haemorrhage	71.21	21.12	28	7998	3051	29563450
Product monitoring error	68.09	21.12	26	8000	2619	29563882
Dizziness	64.69	21.12	152	7874	189532	29376969
Haematoma	57.93	21.12	49	7977	23163	29543338
Cardiac failure	56.33	21.12	87	7939	79200	29487301
International normalised ratio increased	55.12	21.12	64	7962	44308	29522193
Respiratory tract haemorrhage	54.24	21.12	17	8009	947	29565554
Dyspnoea	53.80	21.12	202	7824	326530	29239971
Electrolyte imbalance	53.42	21.12	35	7991	11239	29555262
Platelet dysfunction	51.93	21.12	12	8014	204	29566297
Blood glucose fluctuation	50.68	21.12	23	8003	3574	29562927
Syncope	49.21	21.12	83	7943	81288	29485213
Oedema peripheral	47.87	21.12	94	7932	103463	29463038
Drug ineffective	45.47	21.12	21	8005	363149	29203352
Rectal prolapse	44.17	21.12	11	8015	260	29566241
Blood glucose abnormal	43.13	21.12	23	8003	5060	29561441
Intraductal papillary mucinous neoplasm	41.69	21.12	11	8015	329	29566172
Vena cava injury	41.37	21.12	10	8016	208	29566293
SARS-CoV-2 antibody test positive	40.71	21.12	10	8016	223	29566278
Haematochezia	40.43	21.12	50	7976	36933	29529568
Renal cyst haemorrhage	39.78	21.12	11	8015	394	29566107
Gastrointestinal haemorrhage	36.48	21.12	72	7954	79461	29487040
Fall	35.42	21.12	117	7909	177061	29389440
Arrhythmia	32.09	21.12	41	7985	31272	29535229
Renal failure	31.89	21.12	87	7939	118512	29447989
Spontaneous haemorrhage	31.85	21.12	8	8018	196	29566305
Dyspnoea exertional	31.60	21.12	44	7982	36446	29530055
Gamma-glutamyltransferase increased	30.59	21.12	37	7989	26700	29539801
JC virus CSF test positive	30.34	21.12	7	8019	118	29566383
Language disorder	29.10	21.12	13	8013	1946	29564555
Anaemia	27.09	21.12	117	7909	200834	29365667
Spinal stenosis	26.86	21.12	16	8010	4347	29562154
Carotid arteriosclerosis	26.13	21.12	11	8015	1427	29565074
Urinary incontinence	26.05	21.12	27	7999	16454	29550047
Drug interaction	25.90	21.12	114	7912	197271	29369230
Implant site inflammation	25.74	21.12	6	8020	106	29566395
Mean cell haemoglobin concentration	25.43	21.12	5	8021	37	29566464
Abdominal wall haemorrhage	25.36	21.12	7	8019	249	29566252
Soft tissue haemorrhage	24.59	21.12	6	8020	130	29566371
Cognitive disorder	24.43	21.12	31	7995	23468	29543033
Actinic keratosis	23.61	21.12	14	8012	3772	29562729
Circulatory collapse	23.27	21.12	27	7999	18646	29547855
Nail bed inflammation	23.26	21.12	6	8020	164	29566337
Delayed graft function	23.04	21.12	11	8015	1916	29564585
Orthostatic intolerance	22.55	21.12	8	8018	654	29565847
Prothrombin level decreased	22.30	21.12	9	8017	1049	29565452
Basophil count decreased	21.63	21.12	5	8021	85	29566416
Nocturia	21.56	21.12	18	8008	8344	29558157
Congestive hepatopathy	21.15	21.12	10	8016	1704	29564797

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
General physical health deterioration	375.14	19.80	314	12346	204111	64281961
Product prescribing error	347.16	19.80	159	12501	35110	64450962
Product monitoring error	211.39	19.80	67	12593	5387	64480685
Haematochezia	125.40	19.80	104	12556	66269	64419803
International normalised ratio increased	123.15	19.80	111	12549	79056	64407016
Haematoma	114.43	19.80	85	12575	46165	64439907
Anaemia	105.10	19.80	230	12430	378450	64107622
Drug ineffective	93.54	19.80	25	12635	840222	63645850
Dizziness	83.75	19.80	228	12432	429935	64056137
Cardiac failure	82.36	19.80	115	12545	132258	64353814
Drug interaction	80.76	19.80	202	12458	361881	64124191
Arrhythmia	79.86	19.80	73	12587	52871	64433201
Syncope	79.42	19.80	124	12536	157511	64328561
Atrial fibrillation	78.56	19.80	129	12531	170960	64315112
Dyspnoea	75.49	19.80	309	12351	718365	63767707
International normalised ratio abnormal	73.68	19.80	30	12630	4958	64481114
Bradycardia	70.99	19.80	101	12559	118118	64367954
Fall	68.53	19.80	208	12452	416618	64069454
Electrolyte imbalance	68.31	19.80	49	12611	25194	64460878
Gastrointestinal haemorrhage	62.37	19.80	101	12559	132211	64353861
Labelled drug-drug interaction medication error	53.31	19.80	40	12620	22022	64464050
Respiratory tract haemorrhage	52.44	19.80	17	12643	1467	64484605
Spontaneous haemorrhage	52.40	19.80	13	12647	423	64485649
Therapeutic drug monitoring analysis not performed	51.58	19.80	16	12644	1196	64484876
Pallor	49.92	19.80	49	12611	38732	64447340
Platelet dysfunction	49.53	19.80	12	12648	353	64485719
Oedema peripheral	48.51	19.80	119	12541	210198	64275874
Circulatory collapse	44.12	19.80	43	12617	33689	64452383
Vena cava injury	44.05	19.80	10	12650	220	64485852
Prothrombin time prolonged	43.60	19.80	31	12629	15710	64470362
SARS-CoV-2 antibody test positive	43.26	19.80	10	12650	239	64485833
Intestinal haemorrhage	42.37	19.80	21	12639	5493	64480579
Arthralgia	42.28	19.80	17	12643	442243	64043829
Renal cyst haemorrhage	41.88	19.80	11	12649	451	64485621
Renal failure	41.03	19.80	102	12558	181586	64304486
Intraductal papillary mucinous neoplasm	39.08	19.80	11	12649	586	64485486
Blood loss anaemia	37.65	19.80	27	12633	13865	64472207
Disorientation	36.92	19.80	50	12610	55778	64430294
Language disorder	35.59	19.80	15	12645	2702	64483370
Completed suicide	33.06	19.80	3	12657	224411	64261661
Coagulation test abnormal	32.27	19.80	11	12649	1108	64484964
Foetal chromosome abnormality	32.19	19.80	5	12655	10	64486062
Actinic keratosis	31.96	19.80	17	12643	5148	64480924
Right ventricular failure	31.17	19.80	29	12631	21442	64464630
JC virus CSF test positive	30.88	19.80	7	12653	153	64485919
Painful respiration	30.60	19.80	14	12646	3067	64483005
Electrocardiogram abnormal	29.40	19.80	23	12637	13458	64472614
Contraindicated product administered	29.17	19.80	65	12595	107764	64378308
Dehydration	29.00	19.80	101	12559	216662	64269410
Fracture	28.53	19.80	26	12634	18729	64467343
Overdose	28.34	19.80	82	12578	159484	64326588
Tachycardia	27.67	19.80	78	12582	149501	64336571
Rectal prolapse	27.63	19.80	11	12649	1715	64484357
Mean cell haemoglobin concentration	27.55	19.80	5	12655	33	64486039
Gamma-glutamyltransferase increased	26.97	19.80	40	12620	48470	64437602
Pulmonary vein occlusion	26.48	19.80	6	12654	131	64485941
Aortic arteriosclerosis	26.12	19.80	17	12643	7459	64478613
Blood glucose abnormal	25.72	19.80	18	12642	8895	64477177
Carotid arteriosclerosis	25.65	19.80	11	12649	2068	64484004
Prothrombin level decreased	25.64	19.80	10	12650	1476	64484596
Presyncope	25.62	19.80	33	12627	35056	64451016
Haematuria	25.56	19.80	44	12616	60427	64425645
Prothrombin time shortened	25.36	19.80	12	12648	2837	64483235
Eosinophilic granulomatosis with polyangiitis	25.23	19.80	12	12648	2870	64483202
Rash	25.05	19.80	32	12628	458517	64027555
Vitamin K deficiency	24.89	19.80	8	12652	671	64485401
Spinal stenosis	24.56	19.80	21	12639	13910	64472162
Blood glucose fluctuation	24.46	19.80	15	12645	5940	64480132
Anxiety	24.46	19.80	5	12655	202644	64283428
Epistaxis	24.16	19.80	57	12603	98074	64387998
Abdominal wall haemorrhage	24.09	19.80	7	12653	418	64485654
Drug intolerance	24.06	19.80	4	12656	187988	64298084
Cardiorenal syndrome	23.67	19.80	9	12651	1241	64484831
Implant site inflammation	23.52	19.80	6	12654	219	64485853
Product dose omission issue	23.10	19.80	5	12655	194742	64291330
Off label use	22.99	19.80	57	12603	632749	63853323
Benign prostatic hyperplasia	22.99	19.80	17	12643	9148	64476924
Dyspnoea exertional	22.88	19.80	47	12613	73683	64412389
Melaena	22.68	19.80	39	12621	53509	64432563
Headache	22.25	19.80	44	12616	529423	63956649
Small intestine polyp	22.23	19.80	4	12656	25	64486047
Febrile neutropenia	21.89	19.80	5	12655	187652	64298420
Coagulopathy	21.72	19.80	29	12631	31891	64454181
Delayed graft function	21.67	19.80	11	12649	3025	64483047
Disturbance in attention	21.60	19.80	33	12627	41041	64445031
Cerebral haemorrhage	21.36	19.80	37	12623	51053	64435019
International normalised ratio decreased	21.34	19.80	15	12645	7463	64478609
Accidental underdose	21.04	19.80	7	12653	655	64485417
Abdominal discomfort	20.98	19.80	5	12655	182317	64303755
Soft tissue haemorrhage	20.87	19.80	6	12654	345	64485727
Urogenital haemorrhage	20.85	19.80	7	12653	673	64485399
Hemiparesis	20.15	19.80	27	12633	29800	64456272
Traumatic haemothorax	20.10	19.80	6	12654	394	64485678
Nocturia	20.03	19.80	17	12643	11148	64474924
Product use in unapproved indication	20.02	19.80	5	12655	176613	64309459
Peripheral arterial occlusive disease	19.90	19.80	14	12646	6973	64479099
Haemoptysis	19.83	19.80	35	12625	49013	64437059

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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

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

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

🐶 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:

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

External reference:

ID	Source
4018525	VUID
N0000146847	NUI
D05457	KEGG_DRUG
4018525	VANDF
C0031444	UMLSCUI
CHEBI:50438	CHEBI
CHEMBL1465	ChEMBL_ID
CHEMBL16694	ChEMBL_ID
DB00946	DRUGBANK_ID
D010644	MESH_DESCRIPTOR_UI
54680692	PUBCHEM_CID
6839	IUPHAR_LIGAND_ID
247	INN_ID
Q08SIO485D	UNII
8150	RXNORM
002086	NDDF
59488002	SNOMEDCT_US

Pharmaceutical products:

None