prazosin Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
antihypertensive substances, prazosin derivatives	4209	19216-56-9

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: prazosin prazosin hydrochloride furazosin prazosin HCl	A selective adrenergic alpha-1 antagonist used in the treatment of HEART FAILURE; HYPERTENSION; PHEOCHROMOCYTOMA; RAYNAUD DISEASE; PROSTATIC HYPERTROPHY; and URINARY RETENTION. Molecular weight: 383.41 Formula: C19H21N5O4 CLOGP: 2.03 LIPINSKI: 0 HAC: 9 HDO: 1 TPSA: 106.95 ALOGS: -2.74 ROTB: 4 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Drug dosage:

Dose	Unit	Route
5	mg	O

ADMET properties:

Property	Value	Reference
BDDCS (Biopharmaceutical Drug Disposition Classification System)	1	Benet LZ, Broccatelli F, Oprea TI
S (Water solubility)	1.40 mg/mL	Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine)	0.50 %	Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose)	1.49 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability)	68 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution)	0.73 L/kg	Lombardo F, Berellini G, Obach RS
CL (Clearance)	4.70 mL/min/kg	Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma)	0.06 %	Lombardo F, Berellini G, Obach RS
t_half (Half-life)	2 hours	Lombardo F, Berellini G, Obach RS

Approvals:

Date	Agency	Company	Orphan
June 23, 1976	FDA	PFIZER

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
Hypotension	131.69	57.48	37	188	32399	2325461
Posterior reversible encephalopathy syndrome	77.50	57.48	15	210	2465	2355395
Overdose	76.83	57.48	22	203	19885	2337975
Atrioventricular block first degree	70.53	57.48	12	213	955	2356905
Electrocardiogram QT prolonged	65.44	57.48	16	209	7798	2350062
Acute kidney injury	61.05	57.48	20	205	28102	2329758
Circulatory collapse	60.00	57.48	13	212	3707	2354153
Status epilepticus	59.26	57.48	12	213	2466	2355394
Metabolic acidosis	59.02	57.48	14	211	5984	2351876

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
Priapism	117.22	55.18	22	267	1442	1745050
Hypotension	76.36	55.18	29	260	29625	1716867
Syncope	75.90	55.18	24	265	14145	1732347
Vasoplegia syndrome	72.54	55.18	11	278	191	1746301
Completed suicide	68.55	55.18	23	266	16289	1730203
Acute respiratory distress syndrome	65.87	55.18	16	273	3535	1742957
Aspiration	59.06	55.18	13	276	1857	1744635
Sinus bradycardia	58.63	55.18	13	276	1920	1744572

Pharmacologic Action:

Source	Code	Description
ATC	C02CA01	CARDIOVASCULAR SYSTEM ANTIHYPERTENSIVES ANTIADRENERGIC AGENTS, PERIPHERALLY ACTING Alpha-adrenoreceptor antagonists
ATC	C02LE01	CARDIOVASCULAR SYSTEM ANTIHYPERTENSIVES ANTIHYPERTENSIVES AND DIURETICS IN COMBINATION Alpha-adrenoreceptor antagonists and diuretics
MeSH PA	D018663	Adrenergic Agents
MeSH PA	D058668	Adrenergic alpha-1 Receptor Antagonists
FDA EPC	N0000175553	alpha-Adrenergic Blocker
MeSH PA	D000317	Adrenergic alpha-Antagonists
MeSH PA	D018674	Adrenergic Antagonists
MeSH PA	D000959	Antihypertensive Agents
MeSH PA	D002317	Cardiovascular Agents
MeSH PA	D018377	Neurotransmitter Agents
CHEBI has role	CHEBI:35674	antihypertensive agent
CHEBI has role	CHEBI:37890	alpha-adrenergic antagonist

Drug Use (View source of the data)

Disease	Relation	SNOMED_ID	DOID
Hypertensive disorder	indication	38341003	DOID:10763
Benign prostatic hyperplasia	off-label use	266569009
Chronic Post Traumatic Stress Disorder with Trauma-related Nightmares	off-label use
End stage renal disease	contraindication	46177005	DOID:784
Narcolepsy	contraindication	60380001	DOID:8986
Cataract surgery	contraindication	110473004
Micturition syncope	contraindication	234168001
Syncope	contraindication	271594007
Intraoperative floppy iris syndrome	contraindication	418801006

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	7.22	Basic
pKa2	0.72	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])	Mechanism action	Bioact source	MoA source
Alpha-1A adrenergic receptor	GPCR	P35348	ADA1A_HUMAN	INVERSE AGONIST	Ki	10.40		CHEMBL	IUPHAR
Alpha-1B adrenergic receptor	GPCR	P35368	ADA1B_HUMAN	INVERSE AGONIST	Ki	9.68		CHEMBL	IUPHAR
Alpha-1D adrenergic receptor	GPCR	P25100	ADA1D_HUMAN	INVERSE AGONIST	Ki	9.70		CHEMBL	IUPHAR
5-hydroxytryptamine receptor 2A	GPCR	P28223	5HT2A_HUMAN		Ki	7.73		WOMBAT-PK
Solute carrier family 22 member 1	Transporter	O15245	S22A1_HUMAN		IC50	5		CHEMBL
Solute carrier family 22 member 2	Transporter	O15244	S22A2_HUMAN		IC50	4.87		CHEMBL
Alpha-2A adrenergic receptor	GPCR	P08913	ADA2A_HUMAN		Ki	6.68		CHEMBL
D(4) dopamine receptor	GPCR	P21917	DRD4_HUMAN		Ki	5.08		CHEMBL
5-hydroxytryptamine receptor 1D	GPCR	P28221	5HT1D_HUMAN		Ki	9.48		CHEMBL
Potassium voltage-gated channel subfamily H member 2	Ion channel	Q12809	KCNH2_HUMAN		IC50	5.80		CHEMBL
Alpha-2B adrenergic receptor	GPCR	P18089	ADA2B_HUMAN		Ki	7.89		CHEMBL
Alpha-2C adrenergic receptor	GPCR	P18825	ADA2C_HUMAN		Ki	7.62		CHEMBL
Multidrug and toxin extrusion protein 2	Transporter	Q86VL8	S47A2_HUMAN		IC50	4.42		CHEMBL
Multidrug and toxin extrusion protein 1	Transporter	Q96FL8	S47A1_HUMAN		IC50	5.80		CHEMBL
Adenosine receptor A3	GPCR	P0DMS8	AA3R_HUMAN		IC50	9.07		CHEMBL
Sodium channel alpha subunits; brain (Types I, II, III)	Ion channel	P35498 Q99250 Q9NY46	SCN1A_HUMAN SCN2A_HUMAN SCN3A_HUMAN		IC50	5		CHEMBL
Ribosyldihydronicotinamide dehydrogenase [quinone]	Enzyme	P16083	NQO2_HUMAN		IC50	8.11		CHEMBL
5-hydroxytryptamine receptor 2B	GPCR	P41595	5HT2B_HUMAN		Ki	5.58		DRUG MATRIX
Matrix metalloproteinase-9	Enzyme	P14780	MMP9_HUMAN		IC50	5.16		DRUG MATRIX
Interstitial collagenase	Enzyme	P03956	MMP1_HUMAN		IC50	5.39		DRUG MATRIX
Alpha-1B adrenergic receptor	GPCR		ADA1B_MESAU		Ki	9.08		CHEMBL
Serotonin 2 (5-HT2) receptor	GPCR		5HT2A_RAT 5HT2B_RAT 5HT2C_RAT		IC50	4.38		CHEMBL
Adrenergic receptor alpha-2	GPCR		ADA2A_RAT ADA2B_RAT ADA2C_RAT		Ki	9.40		CHEMBL
Alpha-2A adrenergic receptor	GPCR		ADA2A_RAT		Ki	5.78		CHEMBL
Alpha-1D adrenergic receptor	GPCR		ADA1D_RAT		Ki	9.70		CHEMBL
Alpha-2A adrenergic receptor	GPCR		ADA2A_PIG		Ki	5.39		CHEMBL
Alpha-2 adrenergic receptor	GPCR		ADA2A_MOUSE ADA2B_MOUSE ADA2C_MOUSE		Ki	7.89		CHEMBL
5-hydroxytryptamine receptor 2A	GPCR		5HT2A_RAT		Ki	5.82		CHEMBL
Adrenergic receptor alpha-1	GPCR		ADA1A_RAT ADA1B_RAT ADA1D_RAT		Kd	10.99		CHEMBL
Alpha-1A adrenergic receptor	GPCR		ADA1A_BOVIN		Ki	9.77		CHEMBL
Alpha-2A adrenergic receptor	GPCR		ADA2A_BOVIN		Ki	6.97		CHEMBL
Alpha-1A adrenergic receptor	GPCR		ADA1A_RAT		Ki	10.15		CHEMBL
5-hydroxytryptamine receptor 1A	GPCR		5HT1A_RAT		Ki	5.63		CHEMBL
Alpha-1B adrenergic receptor	GPCR		ADA1B_RAT		Ki	10		CHEMBL
D(2) dopamine receptor	GPCR		DRD2_RAT		IC50	4.96		CHEMBL
Mu-type opioid receptor	GPCR		OPRM_RAT		Ki	9.70		CHEMBL
Beta-casein	Unclassified		CASB_RAT		Ki	9.44		CHEMBL

External reference:

ID	Source
4019901	VUID
N0000147986	NUI
C0032912	UMLSCUI
D00609	KEGG_DRUG
76058001	SNOMEDCT_US
4019901	VANDF
8629	RXNORM
387433003	SNOMEDCT_US
d00138	MMSL
387283005	SNOMEDCT_US
004491	NDDF
CHEMBL2	ChEMBL_ID
CHEMBL1558	ChEMBL_ID
DB00457	DRUGBANK_ID
XRA	PDB_CHEM_ID
CHEBI:8364	CHEBI
X0Z7454B90	UNII
19237-84-4	SECONDARY_CAS_RN
2593	INN_ID
D011224	MESH_DESCRIPTOR_UI
4893	PUBCHEM_CID
503	IUPHAR_LIGAND_ID

Pharmaceutical products:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Minipress	HUMAN PRESCRIPTION DRUG LABEL	1	0069-4310	CAPSULE	1 mg	ORAL	NDA	13 sections
Minipress	HUMAN PRESCRIPTION DRUG LABEL	1	0069-4370	CAPSULE	2 mg	ORAL	NDA	13 sections
Minipress	HUMAN PRESCRIPTION DRUG LABEL	1	0069-4380	CAPSULE	5 mg	ORAL	NDA	13 sections
Prazosin Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0093-4067	CAPSULE	1 mg	ORAL	ANDA	12 sections
Prazosin Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0093-4068	CAPSULE	2 mg	ORAL	ANDA	12 sections
Prazosin Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0093-4069	CAPSULE	5 mg	ORAL	ANDA	12 sections
Prazosin Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0378-1101	CAPSULE	1 mg	ORAL	ANDA	12 sections
Prazosin Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0378-2302	CAPSULE	2 mg	ORAL	ANDA	12 sections
Prazosin Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0378-3205	CAPSULE	5 mg	ORAL	ANDA	12 sections
Prazosin Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	10135-666	CAPSULE	1 mg	ORAL	ANDA	13 sections
Prazosin Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	10135-667	CAPSULE	2 mg	ORAL	ANDA	13 sections
Prazosin Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	10135-668	CAPSULE	5 mg	ORAL	ANDA	13 sections
Prazosin Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	33261-860	CAPSULE	1 mg	ORAL	ANDA	12 sections
Prazosin Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	33261-861	CAPSULE	2 mg	ORAL	ANDA	12 sections
Prazosin Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	43063-248	CAPSULE	5 mg	ORAL	ANDA	12 sections
Prazosin Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	43063-260	CAPSULE	2 mg	ORAL	ANDA	12 sections
Prazosin Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	43353-035	CAPSULE	2 mg	ORAL	ANDA	13 sections
Prazosin Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	43353-868	CAPSULE	2 mg	ORAL	ANDA	13 sections
Prazosin Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	50090-1948	CAPSULE	1 mg	ORAL	ANDA	12 sections
Prazosin Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	51079-630	CAPSULE	1 mg	ORAL	ANDA	12 sections
Prazosin Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	51079-631	CAPSULE	2 mg	ORAL	ANDA	12 sections
Prazosin Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	51079-632	CAPSULE	5 mg	ORAL	ANDA	12 sections
Prazosin Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	53808-1075	CAPSULE	2 mg	ORAL	ANDA	12 sections
Prazosin Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	54868-1547	CAPSULE	2 mg	ORAL	ANDA	12 sections
Prazosin Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	55154-4391	CAPSULE	1 mg	ORAL	ANDA	12 sections
Prazosin Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	55154-8181	CAPSULE	1 mg	ORAL	ANDA	13 sections
Prazosin Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	55289-536	CAPSULE	1 mg	ORAL	ANDA	12 sections
Prazosin	HUMAN PRESCRIPTION DRUG LABEL	1	59762-5310	CAPSULE	1 mg	ORAL	NDA AUTHORIZED GENERIC	13 sections
Prazosin	HUMAN PRESCRIPTION DRUG LABEL	1	59762-5320	CAPSULE	2 mg	ORAL	NDA AUTHORIZED GENERIC	13 sections
Prazosin	HUMAN PRESCRIPTION DRUG LABEL	1	59762-5350	CAPSULE	5 mg	ORAL	NDA AUTHORIZED GENERIC	13 sections