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

Stem definition	Drug id	CAS RN
anticoagulants, dicoumarol derivatives	48	152-72-7

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: G 23350 G-23350 sintrom acenocoumarin nicoumalone acenocoumarol	A coumarin that is used as an anticoagulant. Its actions and uses are similar to those of WARFARIN. (From Martindale, The Extra Pharmacopoeia, 30th ed, p233) Molecular weight: 353.33 Formula: C19H15NO6 CLOGP: 2.64 LIPINSKI: 0 HAC: 8 HDO: 2 TPSA: 106.74 ALOGS: -4.52 ROTB: 5

Molecule

Description

Molfile Inchi Smiles

Synonyms:

G 23350
G-23350
sintrom
acenocoumarin
nicoumalone
acenocoumarol

A coumarin that is used as an anticoagulant. Its actions and uses are similar to those of WARFARIN. (From Martindale, The Extra Pharmacopoeia, 30th ed, p233)

Molecular weight: 353.33
Formula: C19H15NO6
CLOGP: 2.64
LIPINSKI: 0
HAC: 8
HDO: 2
TPSA: 106.74
ALOGS: -4.52
ROTB: 5

Drug dosage:

Dose	Unit	Route
5	mg	O

ADMET properties:

Property	Value	Reference
MRTD (Maximum Recommended Therapeutic Daily Dose)	0.57 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability)	60 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution)	0.24 L/kg	Lombardo F, Berellini G, Obach RS
CL (Clearance)	1.28 mL/min/kg	Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma)	0.02 %	Lombardo F, Berellini G, Obach RS
t_half (Half-life)	7.22 hours	Lombardo F, Berellini G, Obach RS
S (Water solubility)	0.01 mg/mL	Bocci G, Oprea TI, Benet LZ
BDDCS (Biopharmaceutical Drug Disposition Classification System)	2	Bocci G, Oprea TI, Benet LZ

Approvals:

None

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
Drug interaction	631.28	21.53	366	6938	228765	63252953
Hypocoagulable state	250.53	21.53	51	7253	1156	63480562
International normalised ratio increased	225.82	21.53	109	7195	46316	63435402
Torsade de pointes	115.47	21.53	47	7257	13304	63468414
Cardiac failure	114.00	21.53	89	7215	89053	63392665
Upper gastrointestinal haemorrhage	90.73	21.53	44	7260	18808	63462910
Abdominal wall haematoma	86.29	21.53	26	7278	3029	63478689
Muscle haemorrhage	85.27	21.53	26	7278	3153	63478565
Hypomagnesaemia	83.87	21.53	48	7256	28689	63453029
Acute kidney injury	83.05	21.53	125	7179	263290	63218428
Haematoma	80.37	21.53	50	7254	34770	63446948
Erythrodermic psoriasis	72.77	21.53	18	7286	1000	63480718
Bradycardia	72.39	21.53	63	7241	73164	63408554
Atrial fibrillation	66.02	21.53	74	7230	116562	63365156
Retroperitoneal haematoma	62.14	21.53	20	7284	2893	63478825
Cardio-respiratory arrest	62.12	21.53	53	7251	59906	63421812
Anticoagulation drug level above therapeutic	61.97	21.53	17	7287	1418	63480300
Thermohypoaesthesia	61.38	21.53	11	7293	122	63481596
Sight disability	60.58	21.53	11	7293	132	63481586
Electrocardiogram QT prolonged	60.40	21.53	52	7252	59478	63422240
Vascular resistance pulmonary decreased	59.44	21.53	10	7294	74	63481644
Gingival bleeding	59.42	21.53	29	7275	12558	63469160
Hypokalaemia	55.57	21.53	64	7240	103740	63377978
Left-to-right cardiac shunt	54.62	21.53	10	7294	126	63481592
Euphoric mood	48.47	21.53	19	7285	4868	63476850
Gastrointestinal sounds abnormal	48.26	21.53	18	7286	4033	63477685
Subdural haematoma	47.41	21.53	26	7278	14302	63467416
Lower gastrointestinal haemorrhage	45.90	21.53	21	7283	7869	63473849
Haematuria	45.86	21.53	33	7271	29124	63452594
Multimorbidity	44.97	21.53	11	7293	583	63481135
Anaemia	44.87	21.53	102	7202	293328	63188390
Amaurosis	44.70	21.53	11	7293	598	63481120
Hyperkalaemia	44.43	21.53	42	7262	54161	63427557
Stupor	43.74	21.53	17	7287	4258	63477460
Vessel puncture site haemorrhage	42.28	21.53	8	7296	122	63481596
Respiratory tract infection	41.58	21.53	36	7268	41447	63440271
Optic ischaemic neuropathy	41.51	21.53	12	7292	1210	63480508
Hypocalcaemia	41.19	21.53	32	7272	31681	63450037
Haemorrhage intracranial	40.70	21.53	23	7281	13396	63468322
Right ventricular failure	40.44	21.53	25	7279	17163	63464555
Neuromyelitis optica spectrum disorder	38.92	21.53	11	7293	1023	63480695
Syncope	38.72	21.53	57	7247	117328	63364390
Hyponatraemia	37.87	21.53	55	7249	111845	63369873
Disorganised speech	36.73	21.53	11	7293	1254	63480464
Extensor plantar response	36.34	21.53	11	7293	1300	63480418
Pupillary reflex impaired	35.42	21.53	12	7292	2035	63479683
Wound haemorrhage	33.00	21.53	12	7292	2504	63479214
Cardiac failure chronic	32.94	21.53	14	7290	4404	63477314
Mucocutaneous haemorrhage	31.62	21.53	6	7298	93	63481625
Cerebral haemorrhage	31.47	21.53	27	7277	30702	63451016
Pain	31.06	21.53	24	7280	740604	62741114
Acute generalised exanthematous pustulosis	30.92	21.53	18	7286	11081	63470637
Platelet dysfunction	30.82	21.53	6	7298	107	63481611
Haemarthrosis	30.33	21.53	12	7292	3149	63478569
Ventricular tachycardia	30.02	21.53	22	7282	19957	63461761
Serotonin syndrome	28.96	21.53	25	7279	28657	63453061
Neurological decompensation	28.81	21.53	11	7293	2627	63479091
Tetany	27.95	21.53	10	7294	1991	63479727
Rash	26.38	21.53	16	7288	560855	62920863
Drug reaction with eosinophilia and systemic symptoms	25.42	21.53	25	7279	33811	63447907
Transaminases increased	25.11	21.53	24	7280	31343	63450375
Acute leukaemia	25.06	21.53	8	7296	1126	63480592
Dermatitis exfoliative generalised	24.90	21.53	11	7293	3796	63477922
Pyogenic granuloma	24.71	21.53	6	7298	308	63481410
Subdural haemorrhage	23.64	21.53	10	7294	3108	63478610
Ecchymosis	23.25	21.53	15	7289	11079	63470639
Hyperreflexia	23.09	21.53	12	7292	5922	63475796
Metabolic acidosis	22.77	21.53	27	7277	45042	63436676
Conjunctival haemorrhage	22.30	21.53	10	7294	3577	63478141
Disorientation	22.22	21.53	25	7279	39427	63442291
Pulmonary hypertension	21.73	21.53	24	7280	37099	63444619

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
Drug interaction	505.91	19.74	393	6700	225553	34724285
International normalised ratio increased	270.52	19.74	149	6944	47178	34902660
Hypocoagulable state	234.07	19.74	51	7042	895	34948943
Haemorrhage intracranial	193.25	19.74	84	7009	15862	34933976
Cardiac failure	94.52	19.74	104	6989	91144	34858694
Hepatic vein dilatation	71.52	19.74	15	7078	217	34949621
Liver palpable	67.88	19.74	15	7078	281	34949557
Subdural haematoma	61.86	19.74	43	7050	20378	34929460
Anaemia	60.84	19.74	141	6952	233194	34716644
Labelled drug-drug interaction medication error	58.69	19.74	37	7056	14902	34934936
Upper gastrointestinal haemorrhage	57.59	19.74	45	7048	25473	34924365
Haematoma	57.46	19.74	45	7048	25560	34924278
Inferior vena cava dilatation	53.83	19.74	15	7078	745	34949093
Ventricular enlargement	51.16	19.74	14	7079	650	34949188
Atrial enlargement	50.99	19.74	14	7079	658	34949180
Lower gastrointestinal haemorrhage	43.74	19.74	26	7067	9426	34940412
Retroperitoneal haematoma	42.10	19.74	17	7076	2661	34947177
Fixed eruption	41.95	19.74	15	7078	1685	34948153
Acute kidney injury	40.84	19.74	145	6948	304843	34644995
Abdominal wall haematoma	40.81	19.74	15	7078	1822	34948016
Hyperkalaemia	39.76	19.74	59	7034	69330	34880508
Melaena	37.70	19.74	41	7052	35339	34914499
Dyspnoea at rest	36.26	19.74	17	7076	3811	34946027
Epistaxis	35.49	19.74	51	7042	58200	34891638
Spontaneous haematoma	35.40	19.74	10	7083	522	34949316
Chest wall haematoma	34.00	19.74	8	7085	200	34949638
Influenza virus test positive	32.54	19.74	7	7086	115	34949723
Anticoagulation drug level above therapeutic	31.78	19.74	13	7080	2103	34947735
Ejection fraction decreased	31.22	19.74	28	7065	19126	34930712
Lividity	30.44	19.74	7	7086	158	34949680
Rales	30.35	19.74	21	7072	9862	34939976
Gastroduodenal haemorrhage	29.79	19.74	7	7086	174	34949664
Breath sounds abnormal	29.44	19.74	18	7075	6863	34942975
Renal haemorrhage	29.09	19.74	11	7082	1446	34948392
Ventricular tachycardia	28.65	19.74	31	7062	26548	34923290
Immobilisation prolonged	26.77	19.74	4	7089	5	34949833
Electrocardiogram PR prolongation	26.32	19.74	9	7084	886	34948952
Oesophageal adenocarcinoma stage 0	25.97	19.74	4	7089	7	34949831
Atrial tachycardia	25.02	19.74	13	7080	3632	34946206
Cardiac murmur	24.89	19.74	17	7076	7820	34942018
Cardiac failure chronic	24.80	19.74	17	7076	7862	34941976
Muscle haemorrhage	24.77	19.74	13	7080	3705	34946133
Coronary artery stenosis	23.96	19.74	18	7075	9598	34940240
Haematoma muscle	22.59	19.74	9	7084	1359	34948479
Lactic acidosis	21.98	19.74	31	7062	34741	34915097
Orthopnoea	20.94	19.74	13	7080	5090	34944748
Thyroid disorder	20.84	19.74	11	7082	3171	34946667
Subdural haemorrhage	20.81	19.74	11	7082	3180	34946658
Quadrantanopia	20.67	19.74	5	7088	141	34949697
Cardiac ventricular thrombosis	20.45	19.74	8	7085	1152	34948686
Cerebral haemorrhage	20.41	19.74	30	7063	34907	34914931
Blood cyanide increased	20.08	19.74	4	7089	44	34949794
Atrioventricular block	19.89	19.74	15	7078	8048	34941790
Haematuria	19.75	19.74	36	7057	50030	34899808

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
Drug interaction	1039.16	17.91	733	13444	414450	79315761
Hypocoagulable state	462.58	17.91	101	14076	2058	79728153
International normalised ratio increased	441.29	17.91	240	13937	84481	79645730
Haemorrhage intracranial	233.42	17.91	107	14070	26086	79704125
Cardiac failure	203.57	17.91	189	13988	154653	79575558
Upper gastrointestinal haemorrhage	130.57	17.91	85	14092	41295	79688916
Haematoma	126.28	17.91	91	14086	52104	79678107
Abdominal wall haematoma	118.06	17.91	41	14136	4832	79725379
Acute kidney injury	107.78	17.91	265	13912	519139	79211072
Anaemia	100.82	17.91	235	13942	444780	79285431
Subdural haematoma	100.20	17.91	65	14112	31369	79698842
Retroperitoneal haematoma	96.15	17.91	36	14141	5261	79724950
Lower gastrointestinal haemorrhage	87.39	17.91	47	14130	16078	79714133
Anticoagulation drug level above therapeutic	82.11	17.91	29	14148	3591	79726620
Hyperkalaemia	79.83	17.91	100	14077	114298	79615913
Torsade de pointes	79.48	17.91	47	14130	19265	79710946
Hepatic vein dilatation	72.50	17.91	15	14162	233	79729978
Hypomagnesaemia	70.82	17.91	62	14115	46849	79683362
Atrial fibrillation	67.67	17.91	124	14053	197762	79532449
Liver palpable	66.88	17.91	15	14162	346	79729865
Muscle haemorrhage	66.51	17.91	29	14148	6271	79723940
Cardiac failure chronic	64.69	17.91	34	14143	11101	79719110
Haematuria	62.69	17.91	69	14108	68767	79661444
Ventricular tachycardia	60.46	17.91	54	14123	41881	79688330
Gingival bleeding	60.23	17.91	37	14140	16239	79713972
Electrocardiogram QT prolonged	56.74	17.91	75	14102	90311	79639900
Bradycardia	55.51	17.91	92	14085	135465	79594746
Erythrodermic psoriasis	55.29	17.91	18	14159	1740	79728471
Stupor	54.75	17.91	26	14151	6846	79723365
Vascular resistance pulmonary decreased	54.74	17.91	10	14167	77	79730134
Hypokalaemia	54.01	17.91	94	14083	143946	79586265
Inferior vena cava dilatation	53.76	17.91	15	14162	856	79729355
Left-to-right cardiac shunt	52.13	17.91	10	14167	103	79730108
Ventricular enlargement	51.63	17.91	14	14163	718	79729493
Thermohypoaesthesia	51.36	17.91	10	14167	112	79730099
Pain	49.80	17.91	32	14145	703770	79026441
Sight disability	49.78	17.91	10	14167	133	79730078
Labelled drug-drug interaction medication error	48.82	17.91	40	14137	27610	79702601
Syncope	48.63	17.91	102	14075	179347	79550864
Melaena	48.59	17.91	57	14120	60833	79669378
Atrial enlargement	46.73	17.91	14	14163	1029	79729182
Spontaneous haematoma	46.51	17.91	15	14162	1407	79728804
Epistaxis	46.06	17.91	76	14101	111439	79618772
Mucocutaneous haemorrhage	46.04	17.91	10	14167	198	79730013
Ejection fraction decreased	44.90	17.91	42	14135	34535	79695676
Disorganised speech	44.38	17.91	16	14161	2101	79728110
Hypocalcaemia	43.65	17.91	49	14128	49875	79680336
Respiratory tract infection	41.23	17.91	47	14130	48642	79681569
Cerebral haemorrhage	41.13	17.91	51	14126	57622	79672589
Haemarthrosis	40.31	17.91	20	14157	5792	79724419
Joint swelling	39.88	17.91	3	14174	288643	79441568
Cardio-respiratory arrest	39.60	17.91	70	14107	108440	79621771
Immobilisation prolonged	39.51	17.91	8	14169	111	79730100
Fixed eruption	39.20	17.91	16	14161	2938	79727273
Chest wall haematoma	38.39	17.91	10	14167	439	79729772
Hyponatraemia	38.01	17.91	92	14085	177756	79552455
Dyspnoea at rest	36.01	17.91	20	14157	7282	79722929
Gastrointestinal sounds abnormal	35.62	17.91	18	14159	5417	79724794
Vessel puncture site haemorrhage	35.21	17.91	8	14169	196	79730015
Angina pectoris	34.11	17.91	44	14133	51688	79678523
Product dose omission issue	33.01	17.91	3	14174	247534	79482677
Orthopnoea	32.50	17.91	21	14156	10052	79720159
Euphoric mood	32.30	17.91	19	14158	7707	79722504
Drug intolerance	30.82	17.91	5	14172	264114	79466097
Hypotension	30.77	17.91	157	14020	440160	79290051
Arthralgia	30.58	17.91	34	14143	571769	79158442
Neuromyelitis optica spectrum disorder	30.08	17.91	10	14167	1032	79729179
Calciphylaxis	29.23	17.91	14	14163	3756	79726455
Pulmonary hypertension	28.78	17.91	39	14138	48041	79682170
Amaurosis	28.77	17.91	10	14167	1181	79729030
Rash	28.16	17.91	37	14140	578321	79151890
Extensor plantar response	28.11	17.91	11	14166	1810	79728401
Ischaemic stroke	28.07	17.91	32	14145	33099	79697112
Right ventricular failure	27.58	17.91	27	14150	23470	79706741
Disorientation	27.56	17.91	44	14133	62732	79667479
Gastroduodenal haemorrhage	27.34	17.91	7	14170	287	79729924
Multimorbidity	26.92	17.91	10	14167	1429	79728782
Mitral valve incompetence	26.63	17.91	29	14148	28536	79701675
Oesophageal adenocarcinoma stage 0	26.50	17.91	4	14173	7	79730204
Procedural haemorrhage	26.29	17.91	14	14163	4692	79725519
Serotonin syndrome	26.16	17.91	36	14141	44991	79685220
Azotaemia	26.08	17.91	17	14160	8259	79721952
Fatigue	26.06	17.91	82	14095	929645	78800566
Electrocardiogram PR prolongation	25.99	17.91	10	14167	1573	79728638
Influenza virus test positive	25.78	17.91	7	14170	361	79729850
Shock haemorrhagic	25.34	17.91	24	14153	20036	79710175
Mixed liver injury	24.95	17.91	16	14161	7562	79722649
Blood bilirubin increased	24.51	17.91	43	14134	66189	79664022
Lividity	24.34	17.91	7	14170	446	79729765
Atrioventricular block	24.13	17.91	20	14157	14021	79716190
Rectal haemorrhage	23.78	17.91	46	14131	76254	79653957
Swelling	23.36	17.91	5	14172	216706	79513505
Optic ischaemic neuropathy	22.97	17.91	11	14166	2950	79727261
Posthaemorrhagic hydrocephalus	22.91	17.91	4	14173	23	79730188
Ecchymosis	22.74	17.91	20	14157	15186	79715025
Blood loss anaemia	22.41	17.91	20	14157	15478	79714733
Wound haemorrhage	22.18	17.91	12	14165	4149	79726062
Coronary artery stenosis	21.91	17.91	18	14159	12466	79717745
Nasopharyngitis	21.67	17.91	9	14168	253872	79476339
Pupillary reflex impaired	21.67	17.91	11	14166	3342	79726869
International normalised ratio fluctuation	21.36	17.91	11	14166	3443	79726768
Metabolic acidosis	21.27	17.91	46	14131	82483	79647728
Nausea	21.19	17.91	93	14084	957103	78773108
Haematoma muscle	21.15	17.91	10	14167	2605	79727606
Tetany	20.75	17.91	10	14167	2718	79727493
Congestive cardiomyopathy	20.70	17.91	17	14160	11763	79718448
Blood cyanide increased	20.61	17.91	4	14173	44	79730167
Urticaria	20.52	17.91	4	14173	185197	79545014
Platelet dysfunction	20.09	17.91	6	14171	436	79729775
Breath sounds abnormal	19.95	17.91	19	14158	15965	79714246
Infusion related reaction	19.91	17.91	8	14169	230229	79499982
Rales	19.86	17.91	21	14156	19980	79710231
Hepatic cyst ruptured	19.61	17.91	3	14174	6	79730205
Quadrantanopia	19.43	17.91	5	14172	209	79730002
Renal haemorrhage	19.40	17.91	9	14168	2247	79727964
Anxiety	19.37	17.91	10	14167	248502	79481709
Pyogenic granuloma	19.19	17.91	6	14171	509	79729702
Anuria	19.05	17.91	21	14156	20942	79709269
Musculoskeletal stiffness	18.93	17.91	4	14173	175004	79555207
Headache	18.74	17.91	57	14120	653715	79076496
Acute generalised exanthematous pustulosis	18.73	17.91	19	14158	17235	79712976
Atrial tachycardia	18.53	17.91	13	14164	7120	79723091
Acute leukaemia	18.40	17.91	8	14169	1718	79728493
Hypersensitivity	18.38	17.91	12	14165	262227	79467984
Inappropriate antidiuretic hormone secretion	18.32	17.91	23	14154	26290	79703921
Subdural haemorrhage	18.21	17.91	12	14165	5936	79724275
Cardiac ventricular thrombosis	18.19	17.91	8	14169	1765	79728446
Arrhythmia	17.95	17.91	36	14141	61236	79668975

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

Source	Code	Description
ATC	B01AA07	BLOOD AND BLOOD FORMING ORGANS ANTITHROMBOTIC AGENTS ANTITHROMBOTIC AGENTS Vitamin K antagonists
MeSH PA	D000925	Anticoagulants
MeSH PA	D006401	Hematologic Agents
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
Pulmonary embolism	indication	59282003	DOID:9477
Venous thrombosis	indication	111293003

🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	4.96	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])	Mechanism action	Bioact source	MoA source
Vitamin K epoxide reductase complex subunit 1	Enzyme	Q9BQB6	VKOR1_HUMAN	INHIBITOR	IC50	6.11		SCIENTIFIC LITERATURE	SCIENTIFIC LITERATURE
Vitamin K epoxide reductase complex subunit 1	Unclassified		VKOR1_RAT	INHIBITOR	IC50	6.11		IUPHAR

External reference:

ID	Source
N0000167009	NUI
D07064	KEGG_DRUG
154	RXNORM
C0000956	UMLSCUI
CHEBI:53766	CHEBI
CHEMBL397420	ChEMBL_ID
DB01418	DRUGBANK_ID
D000074	MESH_DESCRIPTOR_UI
54676537	PUBCHEM_CID
9015	IUPHAR_LIGAND_ID
503	INN_ID
I6WP63U32H	UNII
387457003	SNOMEDCT_US
79356008	SNOMEDCT_US
002087	NDDF

Pharmaceutical products:

None