Alfuzosin (CED0006529)

Record Information

Version

1.0

Creation Date

2016-05-25 18:19:47 UTC

Update Date

2026-08-20 04:04:25 UTC

Accession Number

CHEM022092

Identification

Common Name

Alfuzosin

Class

Small Molecule

Description

Alfuzosin is an organic compound with the formula C19H27N5O4 and an average molecular weight of 389.45 g/mol. Alfuzosin belongs to the benzodiazines, a subclass of diazanaphthalenes within the organic compounds. This substance functions as an antagonist of three protein targets: the Alpha-1A adrenergic receptor (ADRA1A), the Alpha-1B adrenergic receptor (ADRA1B), and the Alpha-1D adrenergic receptor (ADRA1D). The compound is identified in six recorded sources across various categories. In the realm of healthcare, pharmaceuticals, and veterinary products, it is utilized as a drug for the treatment of benign prostatic hypertrophy. It is also found in household cleaning and consumer products, specifically within tobacco smoke filters, cigar cigarettes, and other smoking requisites. Additionally, it has been detected in indoor air as part of air, dust, and atmospheric transport, as well as in electrically stimulated smoking devices categorized under electrical and electronic equipment. Exposure to alfuzosin occurs through oral and inhalation routes.

Contaminant Type

Human Neurotoxin

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Alfuzosina	ChEBI
Alfuzosine	ChEBI
Alfuzosinum	ChEBI
Xatral	Kegg
Alfusosine	HMDB
N-(3-((4-Amino-6,7-dimethoxy-2-quinazolinyl)methylamino)propyl)tetrahydro-2-furancarboxamide	HMDB
UroXatral	HMDB
Alfusozine	HMDB
Urion	HMDB
Alfuzosin hydrochloride	HMDB
Alphuzosine	HMDB
Alfetim	HMDB
Benestan	HMDB

Chemical Formula

C₁₉H₂₇N₅O₄

Average Molecular Mass

389.449 g/mol

Monoisotopic Mass

389.206 g/mol

CAS Registry Number

81403-80-7

IUPAC Name

N-{3-[(4-amino-6,7-dimethoxyquinazolin-2-yl)(methyl)amino]propyl}oxolane-2-carboxamide

Traditional Name

alfuzosin

SMILES

COC1=C(OC)C=C2C(N)=NC(=NC2=C1)N(C)CCCNC(=O)C1CCCO1

InChI Identifier

InChI=1S/C19H27N5O4/c1-24(8-5-7-21-18(25)14-6-4-9-28-14)19-22-13-11-16(27-3)15(26-2)10-12(13)17(20)23-19/h10-11,14H,4-9H2,1-3H3,(H,21,25)(H2,20,22,23)

InChI Key

WNMJYKCGWZFFKR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quinazolinamines. These are heterocyclic aromatic compounds containing a quianazoline moiety substituted by one or more amine groups.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazanaphthalenes

Sub Class

Benzodiazines

Direct Parent

Quinazolinamines

Alternative Parents

Substituents

Quinazolinamine
Anisole
Dialkylarylamine
Alkyl aryl ether
Aminopyrimidine
Pyrimidine
Imidolactam
Benzenoid
Heteroaromatic compound
Tetrahydrofuran
Carboximidic acid
Carboximidic acid derivative
Dialkyl ether
Ether
Oxacycle
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

monocarboxylic acid amide (CHEBI:51141 )
tetrahydrofuranol (CHEBI:51141 )
quinazolines (CHEBI:51141 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.28 g/L	ALOGPS
logP	2.02	ALOGPS
logP	1.19	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	14.64	ChemAxon
pKa (Strongest Basic)	7.3	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	111.83 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	107.11 m³·mol⁻¹	ChemAxon
Polarizability	42.71 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-00fr-9244000000-7f0f72006d4f335adfd0	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-000i-0009000000-b390e2d32ee38fb79cf9	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00dr-0039000000-1058f618ea52b7aa95e6	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0aos-0195000000-97624e7dcce906c3a1ee	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udi-0391000000-6d58b29a79c5af262723	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udi-1970000000-b3cb9821b3584d86539f	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0i6s-1920000000-50ca3c071a5548796b3a	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-5900000000-b3a86e227650a23790ec	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-9400000000-9929aaf0359abea0c166	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-9100000000-b3dba930d4cfe0d28a8e	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-0009000000-58fd75abdf178ea1b331	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-0119000000-90a7799e494035d224e7	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0abi-5791000000-648d5529faeac9e35dc0	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-9260000000-591f2bacf7d82aeba7e3	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-9250000000-d107a0e9675604325bb1	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-9340000000-f708562f3998488d7fce	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-7910000000-3fe44ce2a42f727569e2	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-05fr-8900000000-dca38c682ad0b6c90b46	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0bvl-9300000000-bad5c36d48e0e93a82aa	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-0249000000-93552ff8c72ff220f172	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-0009000000-58fd75abdf178ea1b331	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udi-1970000000-b0fb2369c6ec0dac4da7	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-000i-0009000000-f7c6ce96d2befa6613a6	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-052o-1689000000-3d4056a0cfaf3a82ba03	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udi-0391000000-32434b3553430d980c1e	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00dr-0039000000-a58e0a0d76403628e0da	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0aos-0195000000-eb21ba4a837e918890c0	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-000i-0009000000-8dc8c9a659cbb0b66e31	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0abi-6791000000-5c785b2846ed0b62783e	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-0119000000-d7c80f8ee62621b1e06e	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-9250000000-46ac706972d35cb89d9b	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-9140000000-1289af78e0fdbba367e5	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-0092000000-4b7c2dae5894c14b8575	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-006x-1090000000-a62c896d99f7b9d73c0a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-3090000000-381d1c6c96f3e65c44e0	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-1139000000-3af55917407f4facdb0b	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00yi-4193000000-b8b9ec6006943f78ab01	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-017i-6390000000-a64c36b6d4e976a6272f	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-0009000000-78a904a53701d2967cf4	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-1029000000-4761f9cb56623d59d64f	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0fs9-1195000000-27de18ebbd71d76a94ec	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-0009000000-7b87d2f62830ce5f72af	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-5097000000-18e8a37e6f5969418d4a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00sj-8192000000-582200abbe9e620dcad6	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
1312.0	Log mg/kg	[740:2300]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
10	Insecticides	Agriculture & land management	Not Available
19	Indoor air	Air, dust & atmospheric transport	Not Available
233	Brushes	Personal care & cosmetics	Not Available
327	Drugs used in benign prostatic hypertrophy	Healthcare, pharmaceuticals & veterinary products	Not Available
518	Electrically Stimulated Smoking Devices	Electrical & Electronic Equipment	Not Available
556	Cigar Cigarettes	Household cleaning & consumer products	Not Available
560	Other Smoking Requisites	Household cleaning & consumer products	Not Available
569	Tobacco Smoke Filters	Household cleaning & consumer products	Not Available
580	Manufacture Preparation Of Tobacco Products	Industrial manufacturing & chemical processing	Not Available
610	Aftersun Products	Personal care & cosmetics	Not Available
611	Anti Perspirants Or Body Deoderants	Personal care & cosmetics	Not Available
632	Apparel	Textiles, leather & furnishings	Not Available

Pathways

1 pathway

Alfuzosin Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Alpha-1A adrenergic receptor	P43140	Rattus norvegicus	Predicted (SEA)	3.11397
Click to view 3D structure	Alpha-1B adrenergic receptor	P15823	Rattus norvegicus	Predicted (SEA)	0.934191
Click to view 3D structure	Alpha-1D adrenergic receptor	P23944	Rattus norvegicus	Predicted (SEA)	2.88042
Click to view 3D structure	Alpha-1A adrenergic receptor	P35348	Humans	Predicted (SEA)	9.73115
Click to view 3D structure	Alpha-1D adrenergic receptor	P25100	Humans	Predicted (SEA)	4.20386
Click to view 3D structure	Alpha-1B adrenergic receptor	P35368	Humans	Predicted (SEA)	6.15009
Click to view 3D structure	Alpha-1A adrenergic receptor	P18130	Bos taurus	Predicted (SEA)	1.94623
Click to view 3D structure	Acetylcholinesterase	P22303	Humans	Predicted (SEA)	54.5723
Click to view 3D structure	D(2) dopamine receptor	P61169	Rat	Predicted (SEA)	139.039
Click to view 3D structure	Alpha-2C adrenergic receptor	P18825	Humans	Predicted (SEA)	82.5202
Click to view 3D structure	Alpha-2B adrenergic receptor	P18089	Humans	Predicted (SEA)	72.0884
Click to view 3D structure	5-hydroxytryptamine receptor 1A	P08908	Humans	Predicted (SEA)	291.623
Click to view 3D structure	5-hydroxytryptamine receptor 1A	P19327	Rattus norvegicus	Predicted (SEA)	213.774
Click to view 3D structure	Alpha-2A adrenergic receptor	P08913	Humans	Predicted (SEA)	140.596
Click to view 3D structure	Alpha-1B adrenergic receptor	P18841	Mesocricetus auratus	Predicted (SEA)	4.43741
Click to view 3D structure	Histone-lysine N-methyltransferase EHMT2	Q96KQ7	Humans	Predicted (SEA)	47.4102
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P14842	Rattus norvegicus	Predicted (SEA)	275.431
Click to view 3D structure	PHD finger protein 19	Q5T6S3	Humans	Predicted (SEA)	11.9109
Click to view 3D structure	Beta-casein	P02665	Rattus norvegicus	Predicted (SEA)	1.86838
Click to view 3D structure	Histone-lysine N-methyltransferase EHMT1	Q9H9B1	Humans	Predicted (SEA)	22.732
Click to view 3D structure	Spindlin-3	Q5JUX0	Humans	Predicted (SEA)	16.2705
Click to view 3D structure	Spindlin-2B	Q9BPZ2	Humans	Predicted (SEA)	16.2705
Click to view 3D structure	Spindlin-4	Q56A73	Humans	Predicted (SEA)	16.2705
Click to view 3D structure	Alpha-1A adrenergic receptor	O02824	Oryctolagus cuniculus	Predicted (SEA)	28.415
Click to view 3D structure	Histone deacetylase 1	Q13547	Humans	Predicted (SEA)	898.38