RAVUCONAZOLE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H17F2N5OS
Molecular Weight	437.465
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@@H](C1=NC(=CS1)C2=CC=C(C=C2)C#N)[C@](O)(CN3C=NC=N3)C4=C(F)C=C(F)C=C4

InChI

InChIKey=OPAHEYNNJWPQPX-RCDICMHDSA-N

InChI=1S/C22H17F2N5OS/c1-14(21-28-20(10-31-21)16-4-2-15(9-25)3-5-16)22(30,11-29-13-26-12-27-29)18-7-6-17(23)8-19(18)24/h2-8,10,12-14,30H,11H2,1H3/t14-,22+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C22H17F2N5OS
Molecular Weight	437.465
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27904057 | https://clinicaltrials.gov/ct2/show/NCT00064311

Ravuconazole is a triazole with antifungal properties that inhibits cytochrome P450 sterol 14a-demethylase, an enzyme involved in sterol synthesis, resulting in lysis of the fungal cell wall and fungal cell death. It was investigated for the treatment of aspergillosis, candidiasis, and onychomycosis, but these studies were discontinued. Ravuconazole is now in phase II clinical trials to investigate efficacy in preventing fungal infections in patients undergoing chemotherapy and stem cell transplantation.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
cytochrome P450 sterol 14a-demethylase 4 Target ID: cytochrome P450 sterol 14a-demethylase Sources: https://www.ncbi.nlm.nih.gov/pubmed/15989596	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Onychomycosis 18 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27904057	Curative	Phase II 1132	Unknown Approved Use Unknown
Fungal infection 21 Sources: https://clinicaltrials.gov/ct2/show/NCT00064311	Preventing	Phase II 1132	Unknown Approved Use Unknown
Invasive aspergillosis 14 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11083644	Curative	Phase II 1132	Unknown Approved Use Unknown

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1587	inhibitor 1767	inhibitor 1852	inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C8 911 OCT2 647 CYP2B6 810 CYP2C19 1478 OAT1 599 CYP3A 214 OAT3 642 OATP1B1 788 P-gp 1461 OATP1B3 706 BCRP 699 MATE1 306 CYP1A2 1524 MATE2-K 9		CYP3A 129 CYP2B 32

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
CYP2B 40	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/16432271/	likely
CYP3A 298	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/16432271/	likely
CYP3A4 1925	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/16432271/	moderate [Ki 1.1 uM]	weak (co-administration study) Comment: Increased Nelfinavir Cmax and AUC by 30.7%, 31.9% (day 2) and decreased by 7.9%, increased by 16.2% (day 29) Sources: https://pubmed.ncbi.nlm.nih.gov/16432271/
CYP1A2 1692	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/29768713/	no
CYP2B6 1001	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/29768713/	no
CYP2D6 1891	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/29768713/	no
MATE1 308	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/29768713/	no
MATE2-K 9	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/29768713/	no
OAT1 603	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/29768713/	no
OAT3 644	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/29768713/	no
OATP1B1 803	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/29768713/	no
OATP1B3 715	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/29768713/	no
BCRP 773	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/29768713/	yes [IC50 1.14 uM]
CYP2C9 1819	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/29768713/	yes [IC50 1.51 uM]
CYP3A 298	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/29768713/	yes [IC50 2.28 uM]
CYP2C8 965	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/29768713/	yes [IC50 2.69 uM]
OCT2 648	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/29768713/	yes [IC50 2.8 uM]
P-gp 1650	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/29768713/	yes [IC50 7.12 uM]
CYP2C19 1553	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/29768713/	yes [IC50 7.49 uM]

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1647	inhibitor 1626 Sources: https://pubmed.ncbi.nlm.nih.gov/24564525/

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P0024L2	https://www.1pchem.com/search?query=1P0024L2
AK Scientific	X5181	https://aksci.com/item_detail.php?cat=X5181
Alfa Chemistry	ACM170864296	http://www.alfa-chemistry.com/search.aspx?q=ACM170864296
Angene	AGN-PC-0QCAH4	http://www.angenechemical.com/productshow/AGN-PC-0QCAH4.html
AstaTech	43027	http://astatechinc.com/CPSResult.php?CRNO=43027
BOC Sciences	170864-29-6	http://www.bocsci.com/description.asp?cas=170864-29-6
BOC Sciences	182760-06-1	http://www.bocsci.com/description.asp?cas=182760-06-1
Capot Chemical	31958	https://www.capotchem.com/search.do?q=31958
Cayman Chemical	18750	http://www.caymanchem.com/app/template/Product.vm/catalog/18750
Chem Scene	CS-6927	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-6927
Hairui	FOSA04001	http://www.hairuichem.com/en/product/search.do?q=FOSA04001
MedChem Express	HY-14272	https://www.medchemexpress.com/search.html?q=HY-14272&ft=&fa=&fp=
MolPort	MolPort-005-935-605	https://www.molport.com/shop/molecule-link/MolPort-005-935-605
MolPort	MolPort-046-069-036	https://www.molport.com/shop/molecule-link/MolPort-046-069-036
MuseChem	R049436	https://www.musechem.com/product/R049436.html
ShangHai Biochempartner	BCP000635	http://www.biochempartner.com/search_BCP000635
ShangHai Biochempartner	BCP05803	http://www.biochempartner.com/search_BCP05803
TargetMol	T7152	https://www.targetmol.com/search?keyword=T7152
Tetrahedron	TS93450	http://www.thsci.com/search.do?q=TS93450
Toronto Research Chemicals	C986750	https://www.trc-canada.com/product-detail/?CatNum=C986750
Toronto Research Chemicals	R128000	https://www.trc-canada.com/product-detail/?CatNum=R128000
Wonderchem	WD05GK9	http://www.wonder-chem.com/search.html?text=WD05GK9
eMolecules	110046822	https://orderbb.emolecules.com/search/#?query=110046822
eMolecules	29936409	https://orderbb.emolecules.com/search/#?query=29936409
eMolecules	300463698	https://orderbb.emolecules.com/search/#?query=300463698
eMolecules	53926975	https://orderbb.emolecules.com/search/#?query=53926975
eNovation Chemicals	D154973	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D154973&searchbtn.x=0&searchbtn.y=0
mcule	MCULE-1506064001	https://mcule.com/MCULE-1506064001/
mcule	MCULE-9138248395	https://mcule.com/MCULE-9138248395/

PubMed

Title	Date	PubMed
Efficacy of ER-30346, a novel oral triazole antifungal agent, in experimental models of aspergillosis, candidiasis, and cryptococcosis.	1996 Oct	8891122
In vitro and in vivo antifungal activities of ER-30346, a novel oral triazole with a broad antifungal spectrum.	1996 Oct	8891121
New azole antifungals. 3. Synthesis and antifungal activity of 3-substituted-4(3H)-quinazolinones.	1998 May 21	9599237
New azole antifungals. 2. Synthesis and antifungal activity of heterocyclecarboxamide derivatives of 3-amino-2-aryl-1-azolyl-2-butanol.	1998 May 21	9599236
In vitro activities of ravuconazole and voriconazole compared with those of four approved systemic antifungal agents against 6,970 clinical isolates of Candida spp.	2002 Jun	12019081
Activities of caspofungin, itraconazole, posaconazole, ravuconazole, voriconazole, and amphotericin B against 448 recent clinical isolates of filamentous fungi.	2003 Aug	12904365
In vitro activity of ravuconazole against 923 clinical isolates of nondermatophyte filamentous fungi.	2005 Dec	16304186
Discovery of novel indazole-linked triazoles as antifungal agents.	2007 Jun 15	17433670

Patents

Sample Use Guides

In Vivo Use Guide

In an asceding oral dose study, single doses of ravuconazole (from 50 to 800 mg once daily)

Route of Administration: Oral

In Vitro Use Guide

Ravuconazole showed very potent in vitro anti-T. cruzi activity with minimal inhibitory concentrations (MIC) of 300 and 1 nM against the extracellular epimastigote and intracellular amastigote forms, respectively.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 17:16:51 GMT 2023` Edited by `admin` on `Sat Dec 16 17:16:51 GMT 2023`
Record UNII	95YH599JWV
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

RAVUCONAZOLE

Official Name

English

Benzonitrile, 4-[2-[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-4-thiazolyl]-

Systematic Name

English

BMS-207147

Code

English

Benzonitrile, 4-[2-[2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-4-thiazolyl]-, [R-(R*,R*)]-

Systematic Name

English

RAVUCONAZOLE [MI]

Common Name

English

RAVUCONAZOLE [MART.]

Common Name

English

ravuconazole [INN]

Common Name

English

Ravuconazole [WHO-DD]

Common Name

English

4-[2-[(1R,2R)-2-(2,4-Difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-4-thiazolyl]benzonitrile

Systematic Name

English

ER-30346

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C514