TRICIRIBINE

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C13H16N6O4
Molecular Weight	320.3039
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1N=C(N)C2=CN([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)C4=NC=NC1=C24

InChI

InChIKey=HOGVTUZUJGHKPL-HTVVRFAVSA-N

InChI=1S/C13H16N6O4/c1-18-11-7-5(10(14)17-18)2-19(12(7)16-4-15-11)13-9(22)8(21)6(3-20)23-13/h2,4,6,8-9,13,20-22H,3H2,1H3,(H2,14,17)/t6-,8-,9-,13-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C13H16N6O4
Molecular Weight	320.3039
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://adisinsight.springer.com/drugs/800001937
Curator's Comment: Description was created based on several sources, including http://www.enzolifesciences.com/BML-EI332/triciribine/ https://www.ncbi.nlm.nih.gov/pubmed/20644979 http://www.apexbt.com/triciribine.html

Triciribine is a purine analogue which inhibits DNA and protein synthesis, it is a synthetic tricyclic nucleoside which acts as a specific inhibitor of the Akt signaling pathway. It selectively inhibits the phosphorylation and activation of Akt1, -2 and -3 but does not inhibit Akt kinase activity nor known upstream Akt activators such as PI 3-Kinase and PDK1. It inhibits cell growth and induces apoptosis preferentially in cells that express aberrant Akt1. In whole cells triciribine is phosphorylated by adenosine kinase which may be necessary for its activity. Triciribine is a cancer drug which was first synthesised in the 1970s and trialled clinically in the 1980s and 1990s without success. Following the discovery in the early 2000s that the drug would be effective against tumours with hyperactivated Akt, it is now again under consideration in a variety of cancers. As PTX-200, the drug is currently in two early stage clinical trials in breast cancer and ovarian cancer being conducted by the small molecule drug development company Prescient Therapeutics.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Serine/threonine-protein kinase AKT 31 Target ID: CHEMBL4282 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20644979	Inhibitor 8504	130.0 nM [IC50]
Human immunodeficiency virus 1 34 Target ID: CHEMBL378 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7685612	Inhibitor 8504	20.0 nM [IC50]
Human immunodeficiency virus 2 3 Target ID: CHEMBL380 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7685612	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Acute leukemia 32 Sources: https://clinicaltrials.gov/ct2/show/NCT02930109	Primary	Phase II 1147	Unknown Approved Use Unknown
Breast cancer 432 Sources: http://adisinsight.springer.com/drugs/800001937	Primary	Phase II 1147	Unknown Approved Use Unknown
Ovarian cancer 160 Sources: http://adisinsight.springer.com/drugs/800001937	Primary	Phase II 1147	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
5.28 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23993427/	15 mg/m² 3 times / 4 weeks multiple, intravenous dose: 15 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered:		TRICIRIBINE PHOSPHATE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
97 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23993427/	15 mg/m² 3 times / 4 weeks multiple, intravenous dose: 15 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered:		TRICIRIBINE PHOSPHATE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
89.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3955547/	55 mg/m² 1 times / day multiple, intravenous dose: 55 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered:		TRICIRIBINE blood	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
27.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23993427/	15 mg/m² 3 times / 4 weeks multiple, intravenous dose: 15 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered:		TRICIRIBINE PHOSPHATE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
350 mg/m2 1 times / 3 weeks multiple, intravenous Highest studied dose Dose: 350 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 350 mg/m2, 1 times / 3 weeks Sources: https://pubmed.ncbi.nlm.nih.gov/6825123	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/6825123	Disc. AE: Liver damage... AEs leading to discontinuation/dose reduction: Liver damage (grade 4-5) Sources: https://pubmed.ncbi.nlm.nih.gov/6825123
30 mg/m2 1 times / day multiple, intravenous MTD Dose: 30 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 30 mg/m2, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8529286	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/8529286	DLT: Hypertriglyceridemia... Dose limiting toxicities: Hypertriglyceridemia (grade 3-4, 10%) Sources: https://pubmed.ncbi.nlm.nih.gov/8529286
55 mg/m2 1 times / week multiple, intravenous MTD Dose: 55 mg/m2, 1 times / week Route: intravenous Route: multiple Dose: 55 mg/m2, 1 times / week Sources: https://pubmed.ncbi.nlm.nih.gov/23993427	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/23993427	Sources: https://pubmed.ncbi.nlm.nih.gov/23993427
40 mg/m2 1 times / day multiple, intravenous Studied dose Dose: 40 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 40 mg/m2, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8529286	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/8529286	DLT: Hyperglycemia... Disc. AE: Hypertriglyceridemia... Dose limiting toxicities: Hyperglycemia (grade 3-4, 60%) AEs leading to discontinuation/dose reduction: Hypertriglyceridemia (grade 3, 20%) Sources: https://pubmed.ncbi.nlm.nih.gov/8529286
65 mg/m2 1 times / week multiple, intravenous Studied dose Dose: 65 mg/m2, 1 times / week Route: intravenous Route: multiple Dose: 65 mg/m2, 1 times / week Sources: https://pubmed.ncbi.nlm.nih.gov/23993427	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/23993427	DLT: Lipase increased, Triglyceride increased... Dose limiting toxicities: Lipase increased (grade 3-4, 28.6%) Triglyceride increased (14.3%) Sources: https://pubmed.ncbi.nlm.nih.gov/23993427

AEs

AE	Significance	Dose	Population
Liver damage	grade 4-5 Disc. AE	350 mg/m2 1 times / 3 weeks multiple, intravenous Highest studied dose Dose: 350 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 350 mg/m2, 1 times / 3 weeks Sources: https://pubmed.ncbi.nlm.nih.gov/6825123	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/6825123
Hypertriglyceridemia	grade 3-4, 10% DLT	30 mg/m2 1 times / day multiple, intravenous MTD Dose: 30 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 30 mg/m2, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8529286	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/8529286
Hypertriglyceridemia	grade 3, 20% Disc. AE	40 mg/m2 1 times / day multiple, intravenous Studied dose Dose: 40 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 40 mg/m2, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8529286	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/8529286
Hyperglycemia	grade 3-4, 60% DLT	40 mg/m2 1 times / day multiple, intravenous Studied dose Dose: 40 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 40 mg/m2, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8529286	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/8529286
Triglyceride increased	14.3% DLT, Disc. AE	65 mg/m2 1 times / week multiple, intravenous Studied dose Dose: 65 mg/m2, 1 times / week Route: intravenous Route: multiple Dose: 65 mg/m2, 1 times / week Sources: https://pubmed.ncbi.nlm.nih.gov/23993427	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/23993427
Lipase increased	grade 3-4, 28.6% DLT, Disc. AE	65 mg/m2 1 times / week multiple, intravenous Studied dose Dose: 65 mg/m2, 1 times / week Route: intravenous Route: multiple Dose: 65 mg/m2, 1 times / week Sources: https://pubmed.ncbi.nlm.nih.gov/23993427	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/23993427

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer

Sourcing

Vendor/Aggregator	ID	URL
AChemBlock	10760	https://aksci.com/item_detail.php?cat=2082AH
AK Scientific	2082AH	https://aksci.com/item_detail.php?cat=2082AH
Angene	AGN-PC-0RBFA3	http://www.angenechemical.com/productshow/AGN-PC-0RBFA3.html
AOBIOUS INC	AOB5912	http://aobious.com/aobious/search?search_query=AOB5912
ApexBio Technology	A8541	https://www.apexbt.com/catalogsearch/result/?q=A8541
AstaTech	C15666	http://astatechinc.com/CPSResult.php?CRNO=C15666
BioSynth	W-202483	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/W-202483
BOC Sciences	35943-35-2	http://www.bocsci.com/description.asp?cas=35943-35-2
Cayman Chemical	10010237	http://www.caymanchem.com/app/template/Product.vm/catalog/10010237
Chem Scene	CS-0968	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0968
ChemShuttle	109829	https://www.chemshuttle.com/catalogsearch/result/?q=109829
Debye Scientific	DB-048898	https://www.debyesci.com/index.php?id=product&ext[cno]=DB-048898
eMolecules	300081155	https://orderbb.emolecules.com/search/#?query=300081155
eMolecules	32234150	https://orderbb.emolecules.com/search/#?query=32234150
eMolecules	44811330	https://orderbb.emolecules.com/search/#?query=44811330
eMolecules	48874327	https://orderbb.emolecules.com/search/#?query=48874327
eMolecules	50580345	https://orderbb.emolecules.com/search/#?query=50580345
eNovation Chemicals	D372509	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D372509&searchbtn.x=0&searchbtn.y=0
Hairui	HR144084	http://www.hairuichem.com/en/product/search.do?q=HR144084
Lab Network	LN01315918	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01315918
Lab Seeker	SC-89664	http://www.labseeker.com/search.php?keywords=SC-89664&category=0
LabSeeker	SC-89664	http://www.labseeker.com/search.php?keywords=SC-89664&category=0
mcule	MCULE-1334932379	https://mcule.com/MCULE-1334932379/
mcule	MCULE-6539598127	https://mcule.com/MCULE-6539598127/
MedChem Express	HY-15457	https://www.medchemexpress.com/search.html?q=HY-15457&ft=&fa=&fp=
Molnova	M14234	https://www.molnova.com/en/serch-list.html?keywords=M14234
MolPort	MolPort-009-019-297	https://www.molport.com/shop/molecule-link/MolPort-009-019-297
MolPort	MolPort-021-805-017	https://www.molport.com/shop/molecule-link/MolPort-021-805-017
MuseChem	I003315	https://www.musechem.com/product/I003315.html
TargetMol	T6065	https://www.targetmol.com/search?keyword=T6065
Tetrahedron	TS61560	http://www.thsci.com/search.do?q=TS61560
Tocris	2151	https://www.tocris.com/search.php?Type=QuickSearch&Value=2151
Toronto Research Chemicals	T774245	https://www.trc-canada.com/product-detail/?CatNum=T774245

PubMed

Title	Date	PubMed
Insulin attenuates arsenic-induced neurite outgrowth impairments by activating the PI3K/Akt/SIRT1 signaling pathway.	2015-08-05	25982963
Piceatannol suppresses the metastatic potential of MCF10A human breast epithelial cells harboring mutated H-ras by inhibiting MMP-2 expression.	2013-10	23877152
Inhibitory roles of prohibitin and chemerin in FSH-induced rat granulosa cell steroidogenesis.	2013-02	23254195
Ursodeoxycholic acid suppresses mitochondria-dependent programmed cell death induced by sodium nitroprusside in SH-SY5Y cells.	2012-02-26	22178905
Preclinical testing of the Akt inhibitor triciribine in T-cell acute lymphoblastic leukemia.	2011-03	20857426
Inhibition of human immunodeficiency virus type 1 by triciribine involves the accessory protein nef.	2010-04	20086149
1-Nitropyrene stabilizes the mRNA of cytochrome P450 1a1, a carcinogen-metabolizing enzyme, via the Akt pathway.	2009-12	19961161
High-throughput screening compatible cell-based assay for interrogating activated notch signaling.	2009-02	19382889
Design, synthesis and antiviral activity of novel 4,5-disubstituted 7-(beta-D-ribofuranosyl)pyrrolo[2,3-d][1,2,3]triazines and the novel 3-amino-5-methyl-1-(beta-D-ribofuranosyl)- and 3-amino-5-methyl-1-(2-deoxy-beta-D-ribofuranosyl)-1,5-dihydro-1,4,5,6,7,8-hexaazaacenaphthylene as analogues of triciribine.	2005-06-02	15916436
Synthesis of new 2'-beta-C-methyl related triciribine analogues as anti-HCV agents.	2004-07-05	15177464
Synthesis and antiviral activity of 2-substituted analogs of triciribine.	2003-12	14714765
Deoxy sugar analogues of triciribine: correlation of antiviral and antiproliferative activity with intracellular phosphorylation.	2000-06-15	10882371
Activity of triciribine and triciribine-5'-monophosphate against human immunodeficiency virus types 1 and 2.	1993-04	7685612

Patents

Sample Use Guides

In Vivo Use Guide

15 mg/m^2 intravenous (IV) Weekly Over 1 Hour On Days 1, 8, and 15.

Route of Administration: Intravenous

In Vitro Use Guide

Triciribine (1 uM) totally inhibited the growth of L1210 cells in culture and caused progressive loss of cellular viability, as indicated by a decreased clonogenicity and nigrosin dye exclusion.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:14:52 GMT 2025` Edited by `admin` on `Mon Mar 31 19:14:52 GMT 2025`
Record UNII	2421HMY9N6
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-154020

Preferred Name

English

TRICIRIBINE

Official Name

English

TCN

Common Name

English

3-AMINO-1,5-DIHYDRO-5-METHYL-1-.BETA.-D-RIBOFURANOSYL-1,4,5,6,8-PENTAAZAACENAPHTHYLENE

Common Name

English

triciribine [INN]

Common Name

English

Triciribine [WHO-DD]

Common Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

249907