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

Stem definition	Drug id	CAS RN
angiotensin-converting enzyme inhibitors	484	62571-86-2

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: captopril (-)-Captopril L-Captopril lopirin S-Captopril SQ14225 SQ-14225 SQ 14225	A potent and specific inhibitor of PEPTIDYL-DIPEPTIDASE A. It blocks the conversion of ANGIOTENSIN I to ANGIOTENSIN II, a vasoconstrictor and important regulator of arterial blood pressure. Captopril acts to suppress the RENIN-ANGIOTENSIN SYSTEM and inhibits pressure responses to exogenous angiotensin. Molecular weight: 217.28 Formula: C9H15NO3S CLOGP: 0.89 LIPINSKI: 0 HAC: 4 HDO: 1 TPSA: 57.61 ALOGS: -1.68 ROTB: 3 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

captopril
(-)-Captopril
L-Captopril
lopirin
S-Captopril
SQ14225
SQ-14225
SQ 14225

A potent and specific inhibitor of PEPTIDYL-DIPEPTIDASE A. It blocks the conversion of ANGIOTENSIN I to ANGIOTENSIN II, a vasoconstrictor and important regulator of arterial blood pressure. Captopril acts to suppress the RENIN-ANGIOTENSIN SYSTEM and inhibits pressure responses to exogenous angiotensin.

Molecular weight: 217.28
Formula: C9H15NO3S
CLOGP: 0.89
LIPINSKI: 0
HAC: 4
HDO: 1
TPSA: 57.61
ALOGS: -1.68
ROTB: 3

Status: OFP

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

Drug dosage:

Dose	Unit	Route
50	mg	O

ADMET properties:

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Property	Value	Reference
BA (Bioavailability)	69 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
EoM (Fraction excreted unchanged in urine)	38 %	Benet LZ, Broccatelli F, Oprea TI
BDDCS (Biopharmaceutical Drug Disposition Classification System)	3	Benet LZ, Broccatelli F, Oprea TI
t_half (Half-life)	2 hours	Lombardo F, Berellini G, Obach RS
MRTD (Maximum Recommended Therapeutic Daily Dose)	19.72 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
S (Water solubility)	160 mg/mL	Benet LZ, Broccatelli F, Oprea TI
CL (Clearance)	12 mL/min/kg	Lombardo F, Berellini G, Obach RS
Vd (Volume of distribution)	0.75 L/kg	Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma)	0.73 %	Lombardo F, Berellini G, Obach RS

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Approvals:

Date	Agency	Company	Orphan
April 6, 1981	FDA	PAR PHARM

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
Segmental diverticular colitis	96.41	14.85	18	11414	156	63477434
Pedal pulse abnormal	95.60	14.85	18	11414	164	63477426
Toxic epidermal necrolysis	86.60	14.85	55	11377	25279	63452311
Calcium ionised decreased	86.10	14.85	18	11414	291	63477299
Blood pressure abnormal	75.50	14.85	42	11390	15156	63462434
Cardiac failure congestive	75.41	14.85	88	11344	92345	63385245
Insulin autoimmune syndrome	70.89	14.85	13	11419	101	63477489
Feeding intolerance	69.65	14.85	18	11414	756	63476834
Reduced facial expression	65.12	14.85	21	11411	1945	63475645
Multiple organ dysfunction syndrome	60.12	14.85	62	11370	56690	63420900

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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
Blood ketone body increased	35.55	14.69	10	8385	433	34948103
Cyanosis	32.68	14.69	26	8369	12738	34935798
Angioedema	28.81	14.69	40	8355	37334	34911202
Hypertensive crisis	27.18	14.69	20	8375	8731	34939805
Cardiac failure congestive	27.13	14.69	61	8334	83209	34865327
Scleroderma renal crisis	26.08	14.69	7	8388	254	34948282
Renal failure	24.57	14.69	78	8317	130479	34818057
Kidney small	23.86	14.69	5	8390	60	34948476
Myocardial infarction	23.39	14.69	73	8322	121012	34827524
Cerebrovascular accident	23.15	14.69	58	8337	84753	34863783

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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
Segmental diverticular colitis	92.96	12.81	18	17372	156	79726842
Pedal pulse abnormal	91.01	12.81	18	17372	176	79726822
Cardiac failure congestive	88.91	12.81	131	17259	142271	79584727
Calcium ionised decreased	71.17	12.81	18	17372	569	79726429
Feeding intolerance	64.35	12.81	18	17372	842	79726156
Myocardial infarction	60.77	12.81	128	17262	184001	79542997
Toxic epidermal necrolysis	58.99	12.81	60	17330	44521	79682477
Insulin autoimmune syndrome	51.15	12.81	13	17377	419	79726579
Reduced facial expression	50.65	12.81	20	17370	2745	79724253
Cyanosis	46.95	12.81	41	17349	25141	79701857

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	C09AA01	CARDIOVASCULAR SYSTEM AGENTS ACTING ON THE RENIN-ANGIOTENSIN SYSTEM ACE INHIBITORS, PLAIN ACE inhibitors, plain
ATC	C09BA01	CARDIOVASCULAR SYSTEM AGENTS ACTING ON THE RENIN-ANGIOTENSIN SYSTEM ACE INHIBITORS, COMBINATIONS ACE inhibitors and diuretics
CHEBI has role	CHEBI:35457	ACE inhibitor
CHEBI has role	CHEBI:35674	antihypertensive drugs
FDA EPC	N0000175562	Angiotensin Converting Enzyme Inhibitor
FDA MoA	N0000000181	Angiotensin-converting Enzyme Inhibitors
MeSH PA	D000806	Angiotensin-Converting Enzyme Inhibitors
MeSH PA	D000959	Antihypertensive Agents
MeSH PA	D002317	Cardiovascular Agents
MeSH PA	D004791	Enzyme Inhibitors

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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
Hypertensive disorder	indication	38341003	DOID:10763
Chronic heart failure	indication	48447003
Diabetic renal disease	indication	127013003
Left ventricular cardiac dysfunction	indication	429589006
Atrial fibrillation	off-label use	49436004	DOID:0060224
Cystinuria	off-label use	85020001	DOID:9266
Diastolic heart failure	off-label use	418304008	DOID:9775
Cystine Renal Calculi	off-label use
Nondiabetic Proteinuric Nephropathy	off-label use
Anuria	contraindication	2472002	DOID:2983

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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	3.85	acidic
pKa2	9.56	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
Angiotensin-converting enzyme	Enzyme	P12821	ACE_HUMAN	INHIBITOR	Ki	8.70	WOMBAT-PK	CHEMBL
Prostaglandin G/H synthase 1	Enzyme	P23219	PGH1_HUMAN		Ki	4.77	CHEMBL
Prothrombin	Enzyme	P00734	THRB_HUMAN		Ki	7.32	CHEMBL
Renin	Enzyme	P00797	RENI_HUMAN		Ki	8.77	CHEMBL
Leukotriene A-4 hydrolase	Enzyme	P09960	LKHA4_HUMAN		IC50	7.15	CHEMBL
Prostaglandin G/H synthase 2	Enzyme	P35354	PGH2_HUMAN		Ki	4.92	CHEMBL
Angiotensin-converting enzyme	Enzyme		ACE_RABIT		Ki	8.77	CHEMBL
Angiotensin-converting enzyme	Enzyme		ACE_RAT		Ki	8.70	CHEMBL
Succinyl-diaminopimelate desuccinylase	Enzyme		DAPE_HAEIN		Ki	5.74	CHEMBL
Beta-lactamase	Enzyme		Q79MP6_PSEAI		Ki	5.62	CHEMBL

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External reference:

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ID	Source
X8Z	PDB_CHEM_ID
000656	NDDF
1998	RXNORM
29439004	SNOMEDCT_US
387160004	SNOMEDCT_US
4017614	VUID
4017614	VANDF
4347	MMSL
4373	INN_ID
44093	PUBCHEM_CID

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Captopril	HUMAN PRESCRIPTION DRUG LABEL	1	0143-1171	TABLET	12.50 mg	ORAL	ANDA	22 sections
Captopril	HUMAN PRESCRIPTION DRUG LABEL	1	0143-1171	TABLET	12.50 mg	ORAL	ANDA	22 sections
Captopril	HUMAN PRESCRIPTION DRUG LABEL	1	0143-1172	TABLET	25 mg	ORAL	ANDA	22 sections
Captopril	HUMAN PRESCRIPTION DRUG LABEL	1	0143-1172	TABLET	25 mg	ORAL	ANDA	22 sections
Captopril	HUMAN PRESCRIPTION DRUG LABEL	1	0143-1173	TABLET	50 mg	ORAL	ANDA	22 sections
Captopril	HUMAN PRESCRIPTION DRUG LABEL	1	0143-1173	TABLET	50 mg	ORAL	ANDA	22 sections
Captopril	HUMAN PRESCRIPTION DRUG LABEL	1	0143-1174	TABLET	100 mg	ORAL	ANDA	22 sections
Captopril	HUMAN PRESCRIPTION DRUG LABEL	1	0143-1174	TABLET	100 mg	ORAL	ANDA	22 sections
Captopril	HUMAN PRESCRIPTION DRUG LABEL	1	0615-4519	TABLET	12.50 mg	ORAL	ANDA	21 sections
Captopril	HUMAN PRESCRIPTION DRUG LABEL	1	0615-4520	TABLET	25 mg	ORAL	ANDA	21 sections

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