Record Information |
---|
Version | 5.0 |
---|
Status | Expected but not Quantified |
---|
Creation Date | 2012-09-06 15:16:50 UTC |
---|
Update Date | 2022-03-07 02:51:46 UTC |
---|
HMDB ID | HMDB0014856 |
---|
Secondary Accession Numbers | |
---|
Metabolite Identification |
---|
Common Name | Adefovir Dipivoxil |
---|
Description | Adefovir Dipivoxil is only found in individuals that have used or taken this drug.Adefovir dipivoxil, previously called bis-POM PMEA, with trade names Preveon and Hepsera, is an orally-administered nucleotide analog reverse transcriptase inhibitor (ntRTI) used for treatment of hepatitis B. It is a failed treatment for HIV. [Wikipedia ]Adefovir dipivoxil is a prodrug of adefovir. Adefovir is an acyclic nucleotide analog of adenosine monophosphate which is phosphorylated to the active metabolite adefovir diphosphate by cellular kinases. Adefovir diphosphate inhibits HBV DNA polymerase (reverse transcriptase) by competing with the natural substrate deoxyadenosine triphosphate and by causing DNA chain termination after its incorporation into viral DNA. The inhibition constant (Ki) for adefovir diphosphate for HBV DNA polymerase was 0.1 μM. Adefovir diphosphate is a weak inhibitor of human DNA polymerases alpha and gamma with Ki values of 1.18 μM and 0.97μM, respectively. |
---|
Structure | CC(C)(C)C(=O)OCOP(=O)(COCCN1C=NC2=C(N)N=CN=C12)OCOC(=O)C(C)(C)C InChI=1S/C20H32N5O8P/c1-19(2,3)17(26)30-11-32-34(28,33-12-31-18(27)20(4,5)6)13-29-8-7-25-10-24-14-15(21)22-9-23-16(14)25/h9-10H,7-8,11-13H2,1-6H3,(H2,21,22,23) |
---|
Synonyms | Value | Source |
---|
Adefovir pivoxil | Kegg | Hepsera | Kegg | Adefovir | HMDB | Adefovirdipivoxl | HMDB | ADV | HMDB | Bis-pom pmea | HMDB | GS-840 | HMDB | PMEA | HMDB | Adefovir depivoxil | HMDB | 9-(2-((-Bis((pivaloyloxy)methoxy)phosphinyl)methoxy)ethyl)adenine | HMDB | Preveon | HMDB |
|
---|
Chemical Formula | C20H32N5O8P |
---|
Average Molecular Weight | 501.4705 |
---|
Monoisotopic Molecular Weight | 501.198849537 |
---|
IUPAC Name | [({[2-(6-amino-9H-purin-9-yl)ethoxy]methyl}({[(2,2-dimethylpropanoyl)oxy]methoxy})phosphoryl)oxy]methyl 2,2-dimethylpropanoate |
---|
Traditional Name | adefovir dipivoxil |
---|
CAS Registry Number | 142340-99-6 |
---|
SMILES | CC(C)(C)C(=O)OCOP(=O)(COCCN1C=NC2=C(N)N=CN=C12)OCOC(=O)C(C)(C)C |
---|
InChI Identifier | InChI=1S/C20H32N5O8P/c1-19(2,3)17(26)30-11-32-34(28,33-12-31-18(27)20(4,5)6)13-29-8-7-25-10-24-14-15(21)22-9-23-16(14)25/h9-10H,7-8,11-13H2,1-6H3,(H2,21,22,23) |
---|
InChI Key | WOZSCQDILHKSGG-UHFFFAOYSA-N |
---|
Chemical Taxonomy |
---|
Description | Belongs to the class of organic compounds known as 6-aminopurines. These are purines that carry an amino group at position 6. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring. |
---|
Kingdom | Organic compounds |
---|
Super Class | Organoheterocyclic compounds |
---|
Class | Imidazopyrimidines |
---|
Sub Class | Purines and purine derivatives |
---|
Direct Parent | 6-aminopurines |
---|
Alternative Parents | |
---|
Substituents | - 6-aminopurine
- Aminopyrimidine
- Dialkyl alkylphosphonate
- Phosphonic acid diester
- Dicarboxylic acid or derivatives
- Imidolactam
- Pyrimidine
- Phosphonic acid ester
- N-substituted imidazole
- Azole
- Heteroaromatic compound
- Imidazole
- Organophosphonic acid derivative
- Amino acid or derivatives
- Carboxylic acid ester
- Carboxylic acid derivative
- Azacycle
- Organophosphorus compound
- Primary amine
- Amine
- Hydrocarbon derivative
- Organic nitrogen compound
- Carbonyl group
- Organic oxide
- Organopnictogen compound
- Organic oxygen compound
- Organooxygen compound
- Organonitrogen compound
- Aromatic heteropolycyclic compound
|
---|
Molecular Framework | Aromatic heteropolycyclic compounds |
---|
External Descriptors | Not Available |
---|
Ontology |
---|
Physiological effect | Not Available |
---|
Disposition | |
---|
Process | |
---|
Role | Not Available |
---|
Physical Properties |
---|
State | Solid |
---|
Experimental Molecular Properties | Property | Value | Reference |
---|
Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.63 g/L | Not Available | LogP | 0.8 | Not Available |
|
---|
Experimental Chromatographic Properties | Not Available |
---|
Predicted Molecular Properties | | Show more...
---|
Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
---|
Adefovir Dipivoxil,1TMS,isomer #1 | CC(C)(C)C(=O)OCOP(=O)(COCCN1C=NC2=C(N[Si](C)(C)C)N=CN=C21)OCOC(=O)C(C)(C)C | 3311.3 | Semi standard non polar | 33892256 | Adefovir Dipivoxil,1TMS,isomer #1 | CC(C)(C)C(=O)OCOP(=O)(COCCN1C=NC2=C(N[Si](C)(C)C)N=CN=C21)OCOC(=O)C(C)(C)C | 3239.4 | Standard non polar | 33892256 | Adefovir Dipivoxil,1TMS,isomer #1 | CC(C)(C)C(=O)OCOP(=O)(COCCN1C=NC2=C(N[Si](C)(C)C)N=CN=C21)OCOC(=O)C(C)(C)C | 5496.1 | Standard polar | 33892256 | Adefovir Dipivoxil,2TMS,isomer #1 | CC(C)(C)C(=O)OCOP(=O)(COCCN1C=NC2=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C21)OCOC(=O)C(C)(C)C | 3275.4 | Semi standard non polar | 33892256 | Adefovir Dipivoxil,2TMS,isomer #1 | CC(C)(C)C(=O)OCOP(=O)(COCCN1C=NC2=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C21)OCOC(=O)C(C)(C)C | 3301.7 | Standard non polar | 33892256 | Adefovir Dipivoxil,2TMS,isomer #1 | CC(C)(C)C(=O)OCOP(=O)(COCCN1C=NC2=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C21)OCOC(=O)C(C)(C)C | 4718.8 | Standard polar | 33892256 | Adefovir Dipivoxil,1TBDMS,isomer #1 | CC(C)(C)C(=O)OCOP(=O)(COCCN1C=NC2=C(N[Si](C)(C)C(C)(C)C)N=CN=C21)OCOC(=O)C(C)(C)C | 3457.5 | Semi standard non polar | 33892256 | Adefovir Dipivoxil,1TBDMS,isomer #1 | CC(C)(C)C(=O)OCOP(=O)(COCCN1C=NC2=C(N[Si](C)(C)C(C)(C)C)N=CN=C21)OCOC(=O)C(C)(C)C | 3411.3 | Standard non polar | 33892256 | Adefovir Dipivoxil,1TBDMS,isomer #1 | CC(C)(C)C(=O)OCOP(=O)(COCCN1C=NC2=C(N[Si](C)(C)C(C)(C)C)N=CN=C21)OCOC(=O)C(C)(C)C | 5392.0 | Standard polar | 33892256 | Adefovir Dipivoxil,2TBDMS,isomer #1 | CC(C)(C)C(=O)OCOP(=O)(COCCN1C=NC2=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C21)OCOC(=O)C(C)(C)C | 3610.2 | Semi standard non polar | 33892256 | Adefovir Dipivoxil,2TBDMS,isomer #1 | CC(C)(C)C(=O)OCOP(=O)(COCCN1C=NC2=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C21)OCOC(=O)C(C)(C)C | 3625.3 | Standard non polar | 33892256 | Adefovir Dipivoxil,2TBDMS,isomer #1 | CC(C)(C)C(=O)OCOP(=O)(COCCN1C=NC2=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C21)OCOC(=O)C(C)(C)C | 4661.5 | Standard polar | 33892256 |
| Show more...
---|
Spectra |
---|
| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
---|
Predicted GC-MS | Predicted GC-MS Spectrum - Adefovir Dipivoxil GC-MS (Non-derivatized) - 70eV, Positive | splash10-0a4j-9715200000-be4793aa3b5324f2d049 | 2017-09-01 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
---|
Experimental LC-MS/MS | LC-MS/MS Spectrum - Adefovir Dipivoxil LC-ESI-qTof , Positive-QTOF | splash10-00b9-0291650000-bfacc10ec3119e8320f0 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Adefovir Dipivoxil , positive-QTOF | splash10-0kfx-1372940000-7cb1aa4d35fd2d90d7b4 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Adefovir Dipivoxil , positive-QTOF | splash10-00b9-0291650000-bfacc10ec3119e8320f0 | 2017-09-14 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Adefovir Dipivoxil 10V, Positive-QTOF | splash10-0udi-1902120000-70d9218f4799e4b06e06 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Adefovir Dipivoxil 20V, Positive-QTOF | splash10-0r09-4902210000-8477053656f9d74eeb50 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Adefovir Dipivoxil 40V, Positive-QTOF | splash10-0a4r-6910000000-ff29d5990721f46c8df5 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Adefovir Dipivoxil 10V, Negative-QTOF | splash10-0f6t-0309020000-13dd87f577f6eae4df2c | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Adefovir Dipivoxil 20V, Negative-QTOF | splash10-0udi-0903000000-3c822353c37c29284a8f | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Adefovir Dipivoxil 40V, Negative-QTOF | splash10-001i-1922000000-607d6864a8d2801ab89f | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Adefovir Dipivoxil 10V, Positive-QTOF | splash10-0udr-5239180000-444adb50df8e9dcc8e3c | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Adefovir Dipivoxil 20V, Positive-QTOF | splash10-0fk9-0096000000-592e65840a6c7d4fec2b | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Adefovir Dipivoxil 40V, Positive-QTOF | splash10-000i-4972000000-f60e4d26bcfe1943e60c | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Adefovir Dipivoxil 10V, Negative-QTOF | splash10-0udi-0429260000-3e0596d28028aed80ce0 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Adefovir Dipivoxil 20V, Negative-QTOF | splash10-0udi-1389000000-87f1f9b00d5ac0c19e44 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Adefovir Dipivoxil 40V, Negative-QTOF | splash10-00di-0090000000-6582070f7152c5e52322 | 2021-10-11 | Wishart Lab | View Spectrum |
| Show more...
---|
Biological Properties |
---|
Cellular Locations | |
---|
Biospecimen Locations | |
---|
Tissue Locations | Not Available |
---|
Pathways | |
---|
Normal Concentrations |
---|
| |
Blood | Expected but not Quantified | Not Quantified | Not Available | Not Available | Taking drug identified by DrugBank entry DB00718 | | details | Urine | Expected but not Quantified | Not Quantified | Not Available | Not Available | Taking drug identified by DrugBank entry DB00718 | | details |
|
---|
Abnormal Concentrations |
---|
| Not Available |
---|
Associated Disorders and Diseases |
---|
Disease References | None |
---|
Associated OMIM IDs | None |
---|
External Links |
---|
DrugBank ID | DB00718 |
---|
Phenol Explorer Compound ID | Not Available |
---|
FooDB ID | Not Available |
---|
KNApSAcK ID | Not Available |
---|
Chemspider ID | 54855 |
---|
KEGG Compound ID | Not Available |
---|
BioCyc ID | Not Available |
---|
BiGG ID | Not Available |
---|
Wikipedia Link | Adefovir |
---|
METLIN ID | Not Available |
---|
PubChem Compound | 60871 |
---|
PDB ID | Not Available |
---|
ChEBI ID | 183515 |
---|
Food Biomarker Ontology | Not Available |
---|
VMH ID | Not Available |
---|
MarkerDB ID | Not Available |
---|
Good Scents ID | Not Available |
---|
References |
---|
Synthesis Reference | Not Available |
---|
Material Safety Data Sheet (MSDS) | Not Available |
---|
General References | - Vazquez E: New drug in expanded access. Posit Aware. 1998 Jan-Feb;9(1):16. [PubMed:11364994 ]
- (). FDA label . .
|
---|