Dexelvucitabine: Difference between revisions

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	{{~~chembox~~		{{Chembox
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		⚫	\| verifiedrevid = 444914527
		⚫	\| ImageFile = Dexelvucitabine.svg
			\| IUPACName = 2′,3′-Didehydro-2′,3′-dideoxy-5-fluorocytidine
		⚫	\| SystematicName = 4-Amino-5-fluoro-1-pyrimidin-2(1''H'')-one
		⚫	\| OtherNames = Reverset
		⚫	\|Section1 = {{Chembox Identifiers
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⚫	\| verifiedrevid = ~~437184543~~
		⚫	\| CASNo = 134379-77-4
⚫	\|ImageFile=Dexelvucitabine.svg
		⚫	\| PubChem = 64973
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⚫	\|~~IUPACName~~=4-Amino-5-fluoro-1-pyrimidin-2-one
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	\| KEGG = D03981		\| KEGG = D03981
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	\| SMILES=C1=CC(OC1CO)N2C=C(C(=NC2=O)N)F
			\| ChemSpiderID = 58498
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			\| ChEMBL = 109831
	\| Formula=C<sub>9</sub>H<sub>10</sub>FN<sub>3</sub>O<sub>3</sub>
			\| SMILES = F\C1=C\N(C(=O)\N=C1\N)/2O(\C=C\2)CO
	\| MolarMass=227.19 g/mol
			\| InChI = 1/C9H10FN3O3/c10-6-3-13(9(15)12-8(6)11)7-2-1-5(4-14)16-7/h1-3,5,7,14H,4H2,(H2,11,12,15)/t5-,7+/m0/s1
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			\| H=10
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			'''Dexelvucitabine''' is a failed experimental agent for the management of ]. It is a ] nucleoside analog and nucleoside ].<ref name=":0" /> that inhibits HIV-1 replication in vitro. During ] there was some indication of a decreased mean viral load in patients with infected human immunodeficiency virus.<ref>{{Cite journal \|last1=Hernandez-Santiago \|first1=Brenda I. \|last2=Mathew \|first2=Judy S. \|last3=Rapp \|first3=Kim L. \|last4=Grier \|first4=Jason P. \|last5=Schinazi \|first5=Raymond F. \|date=June 2007 \|title=Antiviral and Cellular Metabolism Interactions between Dexelvucitabine and Lamivudine \|journal=Antimicrobial Agents and Chemotherapy \|volume=51 \|issue=6 \|pages=2130–2135 \|doi=10.1128/aac.01543-06 \|issn=0066-4804 \|pmc=1891415 \|pmid=17403996}}</ref><ref>{{Cite journal \|last1=Sobieszczyk \|first1=Magdalena E \|last2=Talley \|first2=Angela K \|last3=Wilkin \|first3=Timothy \|last4=Hammer \|first4=Scott M \|date=2005-03-01 \|title=Advances in antiretroviral therapy \|url=https://europepmc.org/article/med/15849370 \|journal=Topics in HIV Medicine \|volume=13 \|issue=1 \|pages=24–44 \|issn=2161-5845 \|pmid=15849370}}</ref>
	'''Dexelvucitabine''' is a failed experimental agent for the treatment of ]. Dexelvucitabine is a cytidine nucleoside analog and nucleoside reverse transcriptase inhibitor. It was found to inhibit HIV-1 replication in vitro and during Phase II clinical trials, it was found to decrease mean viral load in patients with HIV.

	On April 3, 2006, Pharmasset and Incyte ~~Corporation~~, the pharmaceutical companies developing dexelvucitabine announced the decision to cease further trials and development of the drug due to an increased incidence of grade 4 hyperlipasemia in a phase II trial.		On April 3, 2006, ] and ], the pharmaceutical companies developing dexelvucitabine, announced the decision to cease further trials and development of the drug due to an increased incidence of grade 4 hyperlipasemia (an excess of the pancreatic enzyme ] in the bloodstream) in a phase II trial.<ref name=":0">{{Cite web \|last=PubChem \|title=Dexelvucitabine \|url=https://pubchem.ncbi.nlm.nih.gov/compound/64973 \|access-date=2022-04-07 \|website=pubchem.ncbi.nlm.nih.gov \|language=en}}</ref><ref>{{Cite journal \|last=Ryder \|first=Neil S \|date=2007-12-01 \|title=Discontinued drugs in 2006: anti-infectives \|url=https://doi.org/10.1517/13543784.16.12.1867 \|journal=Expert Opinion on Investigational Drugs \|volume=16 \|issue=12 \|pages=1867–1878 \|doi=10.1517/13543784.16.12.1867 \|issn=1354-3784 \|pmid=18041997\|s2cid=40129603 }}</ref>

			==References==
			{{reflist}}


	{{Antiretroviral drug}}		{{Antiretroviral drug}}

	]		]
	]		]
			]
	]		]
			]
			]

Latest revision as of 19:03, 30 April 2023

Dexelvucitabine
Names

IUPAC name 2′,3′-Didehydro-2′,3′-dideoxy-5-fluorocytidine
Systematic IUPAC name 4-Amino-5-fluoro-1-pyrimidin-2(1H)-one
Other names Reverset
Identifiers
CAS Number	134379-77-4
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL109831
ChemSpider	58498
KEGG	D03981
PubChem CID	64973
UNII	KU8SPJ271W
CompTox Dashboard (EPA)	DTXSID20158678
InChI InChI=1S/C9H10FN3O3/c10-6-3-13(9(15)12-8(6)11)7-2-1-5(4-14)16-7/h1-3,5,7,14H,4H2,(H2,11,12,15)/t5-,7+/m0/s1Key: HSBKFSPNDWWPSL-CAHLUQPWSA-N InChI=1/C9H10FN3O3/c10-6-3-13(9(15)12-8(6)11)7-2-1-5(4-14)16-7/h1-3,5,7,14H,4H2,(H2,11,12,15)/t5-,7+/m0/s1Key: HSBKFSPNDWWPSL-CAHLUQPWBD
SMILES F\C1=C\N(C(=O)\N=C1\N)/2O(\C=C\2)CO
Properties
Chemical formula	C₉H₁₀FN₃O₃
Molar mass	227.195 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). N verify (what is ?) Infobox references

Chemical compound

Dexelvucitabine is a failed experimental agent for the management of human immunodeficiency virus infection. It is a cytidine nucleoside analog and nucleoside reverse transcriptase inhibitor. that inhibits HIV-1 replication in vitro. During phase II clinical trials there was some indication of a decreased mean viral load in patients with infected human immunodeficiency virus.

On April 3, 2006, Pharmasset and Incyte, the pharmaceutical companies developing dexelvucitabine, announced the decision to cease further trials and development of the drug due to an increased incidence of grade 4 hyperlipasemia (an excess of the pancreatic enzyme lipase in the bloodstream) in a phase II trial.

References

^ PubChem. "Dexelvucitabine". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-04-07.
Hernandez-Santiago, Brenda I.; Mathew, Judy S.; Rapp, Kim L.; Grier, Jason P.; Schinazi, Raymond F. (June 2007). "Antiviral and Cellular Metabolism Interactions between Dexelvucitabine and Lamivudine". Antimicrobial Agents and Chemotherapy. 51 (6): 2130–2135. doi:10.1128/aac.01543-06. ISSN 0066-4804. PMC 1891415. PMID 17403996.
Sobieszczyk, Magdalena E; Talley, Angela K; Wilkin, Timothy; Hammer, Scott M (2005-03-01). "Advances in antiretroviral therapy". Topics in HIV Medicine. 13 (1): 24–44. ISSN 2161-5845. PMID 15849370.
Ryder, Neil S (2007-12-01). "Discontinued drugs in 2006: anti-infectives". Expert Opinion on Investigational Drugs. 16 (12): 1867–1878. doi:10.1517/13543784.16.12.1867. ISSN 1354-3784. PMID 18041997. S2CID 40129603.

Antiviral drugs: antiretroviral drugs used against HIV (primarily J05)

Capsid inhibitors

Lenacapavir (LEN)

Entry/fusion inhibitors
(Discovery and development)

Integrase inhibitors
(Integrase strand transfer inhibitors (INSTI))

Maturation inhibitors

Protease Inhibitors (PI)
(Discovery and development)

1 generation	Amprenavir (APV) Fosamprenavir (FPV) Indinavir (IDV) Lopinavir (LPV) Nelfinavir (NFV) Ritonavir (RTV) Saquinavir (SQV)
2 generation	Atazanavir (ATV)° Darunavir (DRV)° Tipranavir (TPV) TMC-310911

Reverse-transcriptase
inhibitors (RTIs)

Nucleoside and
nucleotide (NRTI)

Non-nucleoside (NNRTI)
(Discovery and development)

1 generation	Efavirenz (EFV) Nevirapine (NVP) Delavirdine (DLV)
2 generation	diarylpyrimidines Dapivirine (DPV) Etravirine (ETR) Rilpivirine (RPV) Doravirine (DOR) Elsulfavirine (ESV)

Combined formulations

Pharmacokinetic boosters

Experimental agents

Uncoating inhibitors	TRIM5alpha (gene)
Transcription inhibitors	Tat antagonists
Translation inhibitors	Trichosanthin
BNAbs	Elipovimab
Other	Abzyme BIT225 Calanolide A Ceragenin Cyanovirin-N Diarylpyrimidines Epigallocatechin gallate (EGCG) Foscarnet Fosdevirine Griffithsin Hydroxycarbamide KP-1461 Miltefosine Portmanteau inhibitors Scytovirin Seliciclib Synergistic enhancers Tre recombinase Zinc finger protein transcription factor
Failed agents	Aplaviroc Atevirdine Brecanavir Capravirine Dexelvucitabine Droxinavir Lasinavir Emivirine Lersivirine Lodenosine Loviride Mozenavir Palinavir Telinavir

WHO-EM
Withdrawn from market
Clinical trials:
- Phase III
- Never to phase III

°DHHS recommended initial regimen options. Formerly or rarely used agent.

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