ChemFOnt: Showing chemical card for Alprazolam (CFc000008915)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:55:53 UTC

Chemfont ID

CFc000008915

Molecule Identification

Common Name

Alprazolam

Definition

Alprazolam is only found in individuals that have used or taken this drug. It is a triazolobenzodiazepine compound with antianxiety and sedative-hypnotic actions, that is efficacious in the treatment of panic disorders, with or without agoraphobia, and in generalized anxiety disorders. (From AMA Drug Evaluations Annual, 1994, p238)Benzodiazepines bind nonspecifically to benzodiazepine receptors BNZ1, which mediates sleep, and BNZ2, which affects muscle relaxation, anticonvulsant activity, motor coordination, and memory. As benzodiazepine receptors are thought to be coupled to gamma-aminobutyric acid-A (GABA_A) receptors, this enhances the effects of GABA by increasing GABA affinity for the GABA receptor. Binding of the inhibitory neurotransmitter GABA to the site opens the chloride channel, resulting in a hyperpolarized cell membrane that prevents further excitation of the cell.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
8-Chloro-1-methyl-6-phenyl-4H-S-triazolo(4,3-a)(1,4)benzodiazepine	ChEBI
Xanax	ChEBI
TUS-1	HMDB
Alphapharm brand OF alprazolam	HMDB
Alprazolam orion brand	HMDB
Alprazolam pfizer brand	HMDB
Apotex brand OF alprazolam	HMDB
Kalma	HMDB
Kenral brand OF alprazolam	HMDB
Nu alpraz	HMDB
Pfizer brand OF alprazolam	HMDB
Temmler brand OF alprazolam	HMDB
Trankimazin	HMDB
Alprazolam kenral brand	HMDB
Alprazolam novopharm brand	HMDB
Alprazolam nu-pharm brand	HMDB
Apo alpraz	HMDB
Apo-alpraz	HMDB
Arzneimittelwerk dresden brand OF alprazolam	HMDB
Cassadan	HMDB
NuAlpraz	HMDB
Alprazolam alphapharm brand	HMDB
ApoAlpraz	HMDB
Novo alprazol	HMDB
Novo-alprazol	HMDB
NovoAlprazol	HMDB
Nu pharm brand OF alprazolam	HMDB
Nu-pharm brand OF alprazolam	HMDB
Alprazolam apotex brand	HMDB
Alprazolam temmler brand	HMDB
Alprazolan	HMDB
Alprox	HMDB
D-65MT	HMDB
D65MT	HMDB
Esparon	HMDB
Novopharm brand OF alprazolam	HMDB
Nu-alpraz	HMDB
Orion brand OF alprazolam	HMDB
Ralozam	HMDB
Tafil	HMDB

Chemical Formula

C₁₇H₁₃ClN₄

Average Molecular Weight

308.765

Monoisotopic Molecular Weight

308.082874143

IUPAC Name

12-chloro-3-methyl-9-phenyl-2,4,5,8-tetraazatricyclo[8.4.0.0²,⁶]tetradeca-1(10),3,5,8,11,13-hexaene

Traditional Name

neurol

CAS Registry Number

28981-97-7

SMILES

CC1=NN=C2CN=C(C3=CC=CC=C3)C3=C(C=CC(Cl)=C3)N12

InChI Identifier

InChI=1S/C17H13ClN4/c1-11-20-21-16-10-19-17(12-5-3-2-4-6-12)14-9-13(18)7-8-15(14)22(11)16/h2-9H,10H2,1H3

InChI Key

VREFGVBLTWBCJP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1,2,4-triazolo[4,3-a][1,4]benzodiazepines. These are aromatic compounds containing a 1,4-benzodiazepine fused to and sharing a nitrogen atom with a 1,2,4-triazole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodiazepines

Sub Class

1,4-benzodiazepines

Direct Parent

1,2,4-triazolo[4,3-a][1,4]benzodiazepines

Alternative Parents

Substituents

1,2,4-triazolo[4,3-a][1,4]benzodiazepine
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Benzenoid
Azole
1,2,4-triazole
Heteroaromatic compound
Ketimine
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Azacycle
Organopnictogen compound
Organic nitrogen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Imine
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organochlorine compound (CHEBI:2611 )
triazolobenzodiazepine (CHEBI:2611 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0014548)
Membrane (HMDB: HMDB0014548)

Source

Exogenous

Exogenous (HMDB: HMDB0014548)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Anxiolytic drug (HMDB: HMDB0014548)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.032 g/L	ALOGPS
logP	2.23	ALOGPS
logP	2.37	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	18.3	ChemAxon
pKa (Strongest Basic)	5.08	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.07 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	98.88 m³·mol⁻¹	ChemAxon
Polarizability	32.22 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon