Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C4H6N4O3 |
Molecular Weight | 158.1154 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
NC(=O)N[C@H]1NC(=O)NC1=O
InChI
InChIKey=POJWUDADGALRAB-SFOWXEAESA-N
InChI=1S/C4H6N4O3/c5-3(10)6-1-2(9)8-4(11)7-1/h1H,(H3,5,6,10)(H2,7,8,9,11)/t1-/m0/s1
Molecular Formula | C4H6N4O3 |
Molecular Weight | 158.1154 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/19485408Curator's Comment: Description was created based on several sources, including
http://www.akema.it/pdf/allantoin_ctfa.pdf | http://adisinsight.springer.com/drugs/800037582 | https://www.ncbi.nlm.nih.gov/pubmed/16485000 | https://www.ncbi.nlm.nih.gov/pubmed/16462750
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19485408
Curator's Comment: Description was created based on several sources, including
http://www.akema.it/pdf/allantoin_ctfa.pdf | http://adisinsight.springer.com/drugs/800037582 | https://www.ncbi.nlm.nih.gov/pubmed/16485000 | https://www.ncbi.nlm.nih.gov/pubmed/16462750
Allantoin is a metabolic intermediate of a wide variety of organims: from bacteria to vegetals and animals. Allantoin is a skin active ingridient with keratolytic, moisturizing, anti-irritant properties, promotes renewal of epidermal cell and accelerates wounds healing. Allantoin possesses one chiral center thereby exists in the two enantiomeric forms R-(-) and S-( ). Enzymes that catalyze the formation of (S)-allantoin from the product of the urate oxidase reaction have been identified. The two proteins encoded by mouse genes catalyze two consecutive steps following urate oxidation to 5-hydroxyisourate (HIU): hydrolysis of HIU to give 2-oxo-4-hydroxy-4-carboxy-5-ureidoimidazoline (OHCU) and decarboxylation of OHCU to give S-( )-allantoin. Urate oxidation produces racemic allantoin on a time scale of hours, whereas the full enzymatic complement produces dextrorotatory allantoin on a time scale of seconds. Scioderm is developing Allantoin (Zorblisa; SD-101), as a novel topical therapy for patients with epidermolysis bullosa.
CNS Activity
Sources: https://www.google.com/patents/WO2010124185A1
Curator's Comment: No human data available.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: UniProtKB - E3SAZ9 (Allantoin racemase) Sources: https://www.ncbi.nlm.nih.gov/pubmed/237557 |
|||
Target ID: P32375 Gene ID: 854845.0 Gene Symbol: DAL1 Target Organism: Saccharomyces cerevisiae (strain ATCC 204508 / S288c) (Baker's yeast) Sources: https://www.ncbi.nlm.nih.gov/pubmed/18550550/ |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | ZORBLISA Approved UseUnknown |
Doses
Dose | Population | Adverse events |
---|---|---|
6 % 1 times / day multiple, topical (unknown) Studied dose Dose: 6 %, 1 times / day Route: topical Route: multiple Dose: 6 %, 1 times / day Sources: |
unhealthy, ADULT n = 82 Health Status: unhealthy Condition: epidermolysis bullosa Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 82 Sources: |
Other AEs: Pruritus, Urticaria... Other AEs: Pruritus (7.3%) Sources: Urticaria (2.4%) Dry skin (2.4%) Blister (2.4%) wound (2.4%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Blister | 2.4% | 6 % 1 times / day multiple, topical (unknown) Studied dose Dose: 6 %, 1 times / day Route: topical Route: multiple Dose: 6 %, 1 times / day Sources: |
unhealthy, ADULT n = 82 Health Status: unhealthy Condition: epidermolysis bullosa Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 82 Sources: |
Dry skin | 2.4% | 6 % 1 times / day multiple, topical (unknown) Studied dose Dose: 6 %, 1 times / day Route: topical Route: multiple Dose: 6 %, 1 times / day Sources: |
unhealthy, ADULT n = 82 Health Status: unhealthy Condition: epidermolysis bullosa Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 82 Sources: |
Urticaria | 2.4% | 6 % 1 times / day multiple, topical (unknown) Studied dose Dose: 6 %, 1 times / day Route: topical Route: multiple Dose: 6 %, 1 times / day Sources: |
unhealthy, ADULT n = 82 Health Status: unhealthy Condition: epidermolysis bullosa Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 82 Sources: |
wound | 2.4% | 6 % 1 times / day multiple, topical (unknown) Studied dose Dose: 6 %, 1 times / day Route: topical Route: multiple Dose: 6 %, 1 times / day Sources: |
unhealthy, ADULT n = 82 Health Status: unhealthy Condition: epidermolysis bullosa Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 82 Sources: |
Pruritus | 7.3% | 6 % 1 times / day multiple, topical (unknown) Studied dose Dose: 6 %, 1 times / day Route: topical Route: multiple Dose: 6 %, 1 times / day Sources: |
unhealthy, ADULT n = 82 Health Status: unhealthy Condition: epidermolysis bullosa Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 82 Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
Urate to allantoin, specifically (S)-allantoin. | 2006 Mar |
|
Absolute configurations of spiroiminodihydantoin and allantoin stereoisomers: comparison of computed and measured electronic circular dichroism spectra. | 2009 Jun |
|
Characterization of the structure and function of Klebsiella pneumoniae allantoin racemase. | 2011 Jul 15 |
|
Reaction Mechanism and Catalytic Fingerprint of Allantoin Racemase. | 2014 Jul 10 |
|
The Structure and Function of a Microbial Allantoin Racemase Reveal the Origin and Conservation of a Catalytic Mechanism. | 2016 Nov 22 |
Patents
Substance Class |
Chemical
Created
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admin
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Edited
Sat Dec 16 11:00:38 GMT 2023
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Sat Dec 16 11:00:38 GMT 2023
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Record UNII |
XDK458E1J9
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Record Status |
Validated (UNII)
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Record Version |
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