Carboxyamidotriazole Orotate

Synopsis, Chemistry

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Also known as: 187739-60-2, 776c212qqh, Carboxyamidotriazole (orotate), 5-amino-1-[[3,5-dichloro-4-(4-chlorobenzoyl)phenyl]methyl]triazole-4-carboxamide;2,4-dioxo-1h-pyrimidine-6-carboxylic acid, 4-pyrimidinecarboxylic acid, 1,2,3,6-tetrahydro-2,6-dioxo-, compd. with 5-amino-1-((3,5-dichloro-4-(4-chlorobenzoyl)phenyl)methyl)-1h-1,2,3-triazole-4-carboxamide (1:1), 5-amino-1-(3,5-dichloro-4-(4-chlorobenzoyl)benzyl)-1h-1,2,3-triazole-4-carboxamide 2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylate

Molecular Formula

C₂₂H₁₆Cl₃N₇O₆

Molecular Weight

580.8 g/mol

InChI Key

MNWOBDDXRRBONM-UHFFFAOYSA-N

FDA UNII

776C212QQH

Carboxyamidotriazole Orotate is the orotate salt form of carboxyamidotriazole (CAI), an orally bioavailable small molecule with potential antiangiogenic and antiproliferative activities. Carboxyamidotriazole binds to and inhibits non-voltage-operated calcium channels, blocking both Ca2+ influx into cells and Ca2+ release from intracellular stores, resulting in the disruption of calcium channel-mediated signal transduction. CAI inhibits PI3 activity and vascular endothelial growth factor (VEGF) signaling. This may inhibit endothelial proliferation, tumor cell growth, invasion and metastasis.

1 2D Structure

Carboxyamidotriazole Orotate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

5-amino-1-[[3,5-dichloro-4-(4-chlorobenzoyl)phenyl]methyl]triazole-4-carboxamide;2,4-dioxo-1H-pyrimidine-6-carboxylic acid

2.1.2 InChI

InChI=1S/C17H12Cl3N5O2.C5H4N2O4/c18-10-3-1-9(2-4-10)15(26)13-11(19)5-8(6-12(13)20)7-25-16(21)14(17(22)27)23-24-25;8-3-1-2(4(9)10)6-5(11)7-3/h1-6H,7,21H2,(H2,22,27);1H,(H,9,10)(H2,6,7,8,11)

2.1.3 InChI Key

MNWOBDDXRRBONM-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1=CC(=CC=C1C(=O)C2=C(C=C(C=C2Cl)CN3C(=C(N=N3)C(=O)N)N)Cl)Cl.C1=C(NC(=O)NC1=O)C(=O)O

2.2 Other Identifiers

2.2.1 UNII

776C212QQH

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. 187739-60-2

2. 776c212qqh

3. Carboxyamidotriazole (orotate)

4. 5-amino-1-[[3,5-dichloro-4-(4-chlorobenzoyl)phenyl]methyl]triazole-4-carboxamide;2,4-dioxo-1h-pyrimidine-6-carboxylic Acid

5. 4-pyrimidinecarboxylic Acid, 1,2,3,6-tetrahydro-2,6-dioxo-, Compd. With 5-amino-1-((3,5-dichloro-4-(4-chlorobenzoyl)phenyl)methyl)-1h-1,2,3-triazole-4-carboxamide (1:1)

6. 5-amino-1-(3,5-dichloro-4-(4-chlorobenzoyl)benzyl)-1h-1,2,3-triazole-4-carboxamide 2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylate

7. Cto

8. Cai Orotate

9. L-651582 Orotate

10. Unii-776c212qqh

11. Schembl7924972

12. Cai Orotatel-651582 Orotate

13. Ex-a5646

14. Hy-16125

15. Cs-0006151

2.4 Create Date

2006-10-26

3 Chemical and Physical Properties

Molecular Formula	C₂₂H₁₆Cl₃N₇O₆
Molecular Weight	580.8 g/mol
Hydrogen Bond Donor Count	5
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	6
Exact Mass	579.022764 g/mol
Monoisotopic Mass	579.022764 g/mol
Topological Polar Surface Area	212 Å²
Heavy Atom Count	38
Formal Charge	0
Complexity	816
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2