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Details

Stereochemistry ABSOLUTE
Molecular Formula C4H6N4O3
Molecular Weight 158.1154
Optical Activity ( + )
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Allantoin, (S)-

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

HIDE SMILES / InChI

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

Description
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

Curator's Comment: No human data available.

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: UniProtKB - E3SAZ9 (Allantoin racemase)
Target ID: P32375
Gene ID: 854845.0
Gene Symbol: DAL1
Target Organism: Saccharomyces cerevisiae (strain ATCC 204508 / S288c) (Baker's yeast)
Conditions
Doses

Doses

DosePopulationAdverse events​
6 % 1 times / day multiple, topical
Studied dose
Dose: 6 %, 1 times / day
Route: topical
Route: multiple
Dose: 6 %, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Other AEs: Pruritus, Urticaria...
Other AEs:
Pruritus (7.3%)
Urticaria (2.4%)
Dry skin (2.4%)
Blister (2.4%)
wound (2.4%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Blister 2.4%
6 % 1 times / day multiple, topical
Studied dose
Dose: 6 %, 1 times / day
Route: topical
Route: multiple
Dose: 6 %, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Dry skin 2.4%
6 % 1 times / day multiple, topical
Studied dose
Dose: 6 %, 1 times / day
Route: topical
Route: multiple
Dose: 6 %, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Urticaria 2.4%
6 % 1 times / day multiple, topical
Studied dose
Dose: 6 %, 1 times / day
Route: topical
Route: multiple
Dose: 6 %, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
wound 2.4%
6 % 1 times / day multiple, topical
Studied dose
Dose: 6 %, 1 times / day
Route: topical
Route: multiple
Dose: 6 %, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Pruritus 7.3%
6 % 1 times / day multiple, topical
Studied dose
Dose: 6 %, 1 times / day
Route: topical
Route: multiple
Dose: 6 %, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
The Structure and Function of a Microbial Allantoin Racemase Reveal the Origin and Conservation of a Catalytic Mechanism.
2016-11-22
Reaction Mechanism and Catalytic Fingerprint of Allantoin Racemase.
2014-07-10
Characterization of the structure and function of Klebsiella pneumoniae allantoin racemase.
2011-07-15
Absolute configurations of spiroiminodihydantoin and allantoin stereoisomers: comparison of computed and measured electronic circular dichroism spectra.
2009-06
Urate to allantoin, specifically (S)-allantoin.
2006-03
Completing the uric acid degradation pathway through phylogenetic comparison of whole genomes.
2006-03
Patents

Sample Use Guides

In phase 3 trials, Allantoin (Zorblisa; SD-101) was applied topically, once a day to the entire body for 90 days.The typical use of allantoin is between 0.1-0.5% but may be increased up to 2%.
Route of Administration: Topical
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Mon Mar 31 23:34:19 GMT 2025
Edited
by admin
on Mon Mar 31 23:34:19 GMT 2025
Record UNII
XDK458E1J9
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
Allantoin, (S)-
Common Name English
(+)-ALLANTOIN
Preferred Name English
ALLANTOIN, S-(+)-
Common Name English
Urea, N-[(4S)-2,5-dioxo-4-imidazolidinyl]-
Systematic Name English
ALLANTOIN, (+)-
Common Name English
ALLANTOIN S-(+)-FORM [MI]
Common Name English
S-(+)-Allantoin
Common Name English
Code System Code Type Description
DAILYMED
XDK458E1J9
Created by admin on Mon Mar 31 23:34:19 GMT 2025 , Edited by admin on Mon Mar 31 23:34:19 GMT 2025
PRIMARY
EPA CompTox
DTXSID701278152
Created by admin on Mon Mar 31 23:34:19 GMT 2025 , Edited by admin on Mon Mar 31 23:34:19 GMT 2025
PRIMARY
MERCK INDEX
m1520
Created by admin on Mon Mar 31 23:34:19 GMT 2025 , Edited by admin on Mon Mar 31 23:34:19 GMT 2025
PRIMARY Merck Index
CAS
3844-67-5
Created by admin on Mon Mar 31 23:34:19 GMT 2025 , Edited by admin on Mon Mar 31 23:34:19 GMT 2025
PRIMARY
PUBCHEM
439714
Created by admin on Mon Mar 31 23:34:19 GMT 2025 , Edited by admin on Mon Mar 31 23:34:19 GMT 2025
PRIMARY
FDA UNII
XDK458E1J9
Created by admin on Mon Mar 31 23:34:19 GMT 2025 , Edited by admin on Mon Mar 31 23:34:19 GMT 2025
PRIMARY
RXCUI
1739978
Created by admin on Mon Mar 31 23:34:19 GMT 2025 , Edited by admin on Mon Mar 31 23:34:19 GMT 2025
PRIMARY
Related Record Type Details
RACEMATE -> ENANTIOMER