Carboxyamidotriazole

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Carboxyamidotriazole
Names

Preferred IUPAC name 5-Amino-1-{[3,5-dichloro-4-(4-chlorobenzoyl)phenyl]methyl}-1H-1,2,3-triazole-4-carboxamide
Identifiers
CAS Number	99519-84-3^Y
3D model (JSmol)	Interactive image
ChemSpider	97232^N
ECHA InfoCard	100.231.281
EC Number	804-580-3
PubChem CID	108144
UNII	6ST3ZF52WB^Y
CompTox Dashboard (EPA)	DTXSID40244108
InChI InChI=1S/C17H12Cl3N5O2/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/h1-6H,7,21H2,(H2,22,27)^N Key: WNRZHQBJSXRYJK-UHFFFAOYSA-N^N InChI=1/C17H12Cl3N5O2/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/h1-6H,7,21H2,(H2,22,27) Key: WNRZHQBJSXRYJK-UHFFFAOYAY
SMILES C1=CC(=CC=C1C(=O)C2=C(C=C(C=C2Cl)CN3C(=C(N=N3)C(=O)N)N)Cl)Cl
Properties
Chemical formula	C₁₇H₁₂Cl₃N₅O₂
Molar mass	424.66848
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references

Carboxyamidotriazole is a calcium channel blocker that blocks voltage-gated and ligand-gated calcium channels and has been investigated as an anti-cancer drug in vitro.^[1]^[2]

References

^ Figg, W. D.; Cole, K. A.; Reed, E.; Steinberg, S. M.; Piscitelli, S. C.; Davis, P. A.; Soltis, M. J.; Jacob, J.; Boudoulas, S.; Goldspiel, B. (1995). "Pharmacokinetics of orally administered carboxyamido-triazole, an inhibitor of calcium-mediated signal transduction". Clinical Cancer Research. 1 (8): 797–803. PMID 9816048.
^ Bonnefond, M. L.; Florent, R.; Lenoir, S.; Lambert, B.; Abeilard, E.; Giffard, F.; Louis, M. H.; Elie, N.; Briand, M.; Vivien, D.; Poulain, L.; Gauduchon, P.; n'Diaye, M. (2018). "Inhibition of store-operated channels by carboxyamidotriazole sensitizes ovarian carcinoma cells to anti-BCLX_L strategies through MCL-1 down-regulation". Oncotarget. 9 (74): 33896–33911. doi:10.18632/oncotarget.26084. PMC 6188062. PMID 30338034.

Ion channel modulators

Calcium

VDCCs

Blockers

L-type-selective: Dihydropyridines: Amlodipine
Aranidipine
Azelnidipine
Barnidipine
Clevidipine
Cronidipine
Darodipine
Dexniguldipine
Elgodipine
Elnadipine
Felodipine
Flordipine
Furnidipine
Iganidipine
Isradipine
Lacidipine
Lemildipine
Lercanidipine
Levamlodipine
Levniguldipine
Manidipine
Mepirodipine
Mesudipine
Nicardipine
Nifedipine
Niguldipine
Niludipine
Nilvadipine
Nimodipine
Nisoldipine
Nitrendipine
Olradipine
Oxodipine
Palonidipine
Pranidipine
Ryodipine (riodipine)
Sagandipine
Sornidipine
Teludipine
Tiamdipine
Trombodipine
Vatanidipine; Diltiazem derivatives: Clentiazem
Diltiazem
Iprotiazem
Nictiazem
Siratiazem; Phenylalkylamines: Anipamil
Dagapamil
Devapamil
Dexverapamil
Emopamil
Etripamil
Falipamil
Gallopamil
Levemopamil
Nexopamil
Norverapamil
Ronipamil
Tiapamil
Verapamil; Others: AH-1058
Brinazarone
Budiodarone
Celivarone
Cyproheptadine
Dronedarone
Fantofarone
SR-33805
Tetrahydropalmatine

R-type-selective: SNX-482

α₂δ subunit-selective (gabapentinoids): 4-Methylpregabalin
Arbaclofen
Arbaclofen placarbil
Atagabalin
Baclofen
Gabapentin
Gabapentin enacarbil
Imagabalin
Mirogabalin
PD-200,347
PD-217,014
PD-299,685
Phenibut
Pregabalin

Activators

L-type-selective: Bay K8644

Potassium

VGKCs

Blockers

hERG (KCNH2, K_v11.1)-specific: Ajmaline
Amiodarone
AmmTX3
Astemizole
Azaspiracid
AZD1305
Azimilide
Bedaquiline
BeKm-1
BmTx3
BRL-32872
Chlorpromazine
Cisapride
Clarithromycin
Darifenacin
Dextropropoxyphene
Diallyl trisulfide
Domperidone
E-4031
Ergtoxins
Erythromycin
Gigactonine
Haloperidol
Ketoconazole
Norpropoxyphene
Orphenadrine
Pimozide
PNU-282,987
Promethazine
Quinidine
Ranolazine
Roxithromycin
Sertindole
Solifenacin
Tamulotoxin
Terodiline
Terfenadine
Thioridazine
Tolterodine
Vanoxerine
Vernakalant

Activators

KCNQ (K_v7)-specific: Flupirtine
Retigabine

IRKs

Blockers

K_ATPTooltip ATP-sensitive potassium channel-specific: Acetohexamide
Carbutamide
Chlorpropamide
Glibenclamide (glyburide)
Glibornuride
Glicaramide
Gliclazide
Glimepiride
Glipizide
Gliquidone
Glisoxepide
Glyclopyramide
Glycyclamide
Metahexamide
Mitiglinide
Nateglinide
Repaglinide
Tolazamide
Tolbutamide

GIRKTooltip G protein-coupled inwardly rectifying potassium channel-specific: Barium
Caramiphen
Cloperastine
Clozapine
Dextromethorphan
Ethosuximide
Ifenprodil
Tertiapin
Tipepidine

Activators

K_ATPTooltip ATP-sensitive potassium channel-specific: Aprikalim
Bimakalim
Cromakalim
Diazoxide
Emakalim
Levcromakalim
Mazokalim
Minoxidil
Minoxidil sulfate
Naminidil
Nicorandil
Pinacidil
Rilmakalim
Sarakalim

GIRKTooltip G protein-coupled inwardly rectifying potassium channel-specific: ML-297 (VU0456810)

K_Ca

Blockers	BK_Ca-specific: Ethanol (alcohol) GAL-021
Activators	BK_Ca-specific: Flufenamic acid Meclofenamic acid Niflumic acid Nimesulide Rottlerin (mallotoxin) Tolfenamic acid

K2Ps

Blockers	12-O-Tetradecanoylphorbol-13-acetate Arachidonic acid Fluoxetine Norfluoxetine
Activators	Riluzole

Sodium

VGSCs

Blockers

Antianginals: Ranolazine

Local anesthetics: pFBT
Amylocaine
Articaine
Benzocaine
Bupivacaine (Levobupivacaine, Ropivacaine)
Butacaine
Butamben
Chloroprocaine
Cinchocaine
Cocaine
Cyclomethycaine
Dimethocaine
Diphenhydramine
Etidocaine
Hexylcaine
Iontocaine
Lidocaine
Mepivacaine
Meprylcaine
Metabutoxycaine
Orthocaine
Piperocaine
Prilocaine
Procaine
Propoxycaine
Proxymetacaine
Risocaine
Tetracaine
Trimecaine

Activators

Aconitine
Atracotoxins (ω-Atracotoxin, Robustoxin, Versutoxin)
Batrachotoxin
Ciguatoxins
Grayanotoxins
Poneratoxin

ENaC

Blockers	Amiloride Benzamil Triamterene
Activators	Solnatide

ASICs

Blockers	A-317567 Amiloride Aspirin Ibuprofen PcTX1

Chloride

CaCCs

Blockers	Crofelemer DIDS Ethacrynic acid Flufenamic acid Fluoxetine Furosemide Glibenclamide Mefloquine Mibefradil Niflumic acid
Activators	Carbachol

CFTR

Blockers	Glibenclamide Lonidamine Piretanide
Activators	1,7-Phenanthroline 1,10-Phenanthroline 4,7-Phenanthroline 7,8-Benzoquinoline Ivacaftor Phenanthridine

Unsorted

Blockers	Bumetanide Flufenamic acid Meclofenamic acid Mefenamic acid Mepacrine Niflumic acid Talniflumate Tolfenamic acid Trifluoperazine

Others

TRPsTooltip Transient receptor potential channels	See here instead.
LGICsTooltip Ligand gated ion channels	See here instead.

See also: Receptor/signaling modulators • Transient receptor potential channel modulators

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