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Details

Stereochemistry ABSOLUTE
Molecular Formula C3H6O3
Molecular Weight 90.0779
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LACTIC ACID, L-

SMILES

C[C@H](O)C(O)=O

InChI

InChIKey=JVTAAEKCZFNVCJ-REOHCLBHSA-N
InChI=1S/C3H6O3/c1-2(4)3(5)6/h2,4H,1H3,(H,5,6)/t2-/m0/s1

HIDE SMILES / InChI
Lactic Acid, L- (L-lactic acid, L-lactate) is the levorotatory isomer of lactic acid, the biologically active isoform in humans. Lactic acid or lactate is produced during fermentation from pyruvate by lactate dehydrogenase. Lactate dehydrogenase is isomer-specific so that production and metabolism of D-lactate require D-LDH and L-lactate requires L-LDH. Mammalian cells only contain L-LDH so that in humans the lactate produced is almost exclusively L-lactate. Carbohydrate-fermenting bacterial species (e.g. lactobacillus spp) have by contrast both enzymes and therefore the capacity to produce both D-lactate and L-lactate. L-lactic acid is the primary agonist of hydroxycarboxylic acid receptor 1 (HCA1), which is a Gi/o-coupled G protein-coupled receptor (GPCR). Poly-L-lactic acid is an absorbable, semi-permanent, injectable implant that can be used to restore volume and stimulate collagen formation gradually. It is FDA-approved for the correction of facial fat loss associated with antiretroviral therapy-induced lipoatrophy in HIV patients. It is FDA-approved for use in immunocompetent people for the correction of nasolabial fold deficiencies and other facial wrinkles. It has been used off-label to enhance the cheeks, hands, neck, thighs, gluteal enhancement and chest wall deformities, such as pectus excavatum or thoracic deformities secondary to surgical procedures.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q9BXC0
Gene ID: 27198.0
Gene Symbol: HCAR1
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
PRISMASOL

Approved Use

PRISMASOL solution is indicated as a replacement solution in Continuous Renal Replacement Therapy (CRRT) and in case of drug poisoning when CRRT is used to remove dialyzable substances.

Launch Date

2006
PubMed

PubMed

TitleDatePubMed
High resolution 1H n.m.r. studies of vertebrate blood and plasma.
1983 Jun 1
1H NMR characterization of normal human cerebrospinal fluid and the detection of methylmalonic acid in a vitamin B12 deficient patient.
1991 Aug
Physiology and pathophysiology of organic acids in cerebrospinal fluid.
1993
Lactate and pyruvate concentrations in capillary blood from newborns.
1994 Sep
Intracellular flux analysis applied to the effect of dissolved oxygen on hybridomas.
1995 Dec
Standardized method for high-resolution 1H-NMR of cerebrospinal fluid.
1995 May
Abnormal substrate levels that depend upon mitochondrial function in cerebrospinal fluid from Alzheimer patients.
1998
Paraquat-induced renal injury studied by 1H nuclear magnetic resonance spectroscopy of urine.
1998 Jun
L-lactic acid as a mosquito (Diptera: Culicidae) repellent on human and mouse skin.
2001 Jan
The 12,13-diol cyclization approach for a truly stereocontrolled total synthesis of epothilone B and the synthesis of a conformationally restrained analogue.
2001 May 18
Diastereomeric salts of lactic acid and 1-phenylethylamine, their structures and relative stabilities.
2002 Dec
Asymmetric intramolecular [2 + 2] photocycloadditions: alpha- and beta-hydroxy acids as chiral tether groups.
2002 Feb 22
Asymmetric total synthesis of (+)-brefeldin A from (S)-lactate by triple chirality transfer process and nitrile oxide cycloaddition.
2002 Feb 8
1H and (13)C NMR spectroscopic analysis of human saliva.
2002 Jun
RIO: analyzing proteomes by automated phylogenomics using resampled inference of orthologs.
2002 May 16
Synthesis of optically active atropisomeric anilide derivatives through diastereoselective N-allylation with a chiral Pd-pi-allyl catalyst.
2003 Dec 12
The absolute configuration of 1-carboxyethyl substituents on common hexoses by circular dichroism.
2003 Jan 2
Structure of the O-polysaccharide of Proteus penneri 28 and Proteus vulgaris O31 and classification of P. penneri 26 and 28 in Proteus serogroup O31.
2003 Oct 24
In vivo and in vitro nuclear magnetic resonance spectroscopy as a tool for investigating hepatobiliary disease: a review of H and P MRS applications.
2005 Apr
Asymmetric intermolecular C-H functionalization of benzyl silyl ethers mediated by chiral auxiliary-based aryldiazoacetates and chiral dirhodium catalysts.
2005 Dec 23
Proton MR CSF analysis and a new software as predictors for the differentiation of meningitis in children.
2005 Jun
Dynamic simulation of red blood cell metabolism and its application to the analysis of a pathological condition.
2005 May 9
Automated no-carrier-added synthesis of [1-11C]-labeled D- and L-enantiomers of lactic acid.
2006 Dec
Plasma concentrations and urinary excretion of purine bases (uric acid, hypoxanthine, and xanthine) and oxypurinol after rigorous exercise.
2006 Jan
Remote ischaemic preconditioning protects against cardiopulmonary bypass-induced tissue injury: a preclinical study.
2006 Oct
Non-Hodgkin's lymphomas: immunologic prognostic studies.
2007 Jul
Role of GPR81 in lactate-mediated reduction of adipose lipolysis.
2008 Dec 19
Facile alcoholysis of L-lactide catalysed by Group 1 and 2 metal complexes.
2008 Jun 21
Design of a "new motif" with beta-amino acids and alpha-aminoxy acids: synthesis of hybrid peptides with 12/10-helix.
2008 May 16
Overcoming extractability hurdles of a 14C labeled taxane analogue milataxel and its metabolite from xenograft mouse tumor and brain tissues.
2009 Apr 5
Examination of the biological role of the alpha(2-->6)-linked sialic acid in gangliosides binding to the myelin-associated glycoprotein (MAG).
2009 Feb 26
Lactate inhibits lipolysis in fat cells through activation of an orphan G-protein-coupled receptor, GPR81.
2009 Jan 30
Serum amyloid A as a prognostic marker in melanoma identified by proteomic profiling.
2009 May 1
Studies on the biodegradation of fosfomycin: growth of Rhizobium huakuii PMY1 on possible intermediates synthesised chemically.
2009 May 7
An autocrine lactate loop mediates insulin-dependent inhibition of lipolysis through GPR81.
2010 Apr 7
Characterization of a diverse secretome generated by the mouse preimplantation embryo in vitro.
2010 Jun 23
Perioperative chronic use of statins and the risk of muscle complaints in patients undergoing knee and hip endoprosthesis surgery.
2010 Mar
Screening β-arrestin recruitment for the identification of natural ligands for orphan G-protein-coupled receptors.
2013 Jun
Patents

Sample Use Guides

Facial fat loss (lipoatrophy) Sculptra (Poly-L-lactic acid): Intradermal or SubQ: ~0.05-0.2 mL per individual injection depending on technique used; ~20 injections may be needed per cheek. Treatment should be individualized. Separate treatments by ≥2 weeks. Typical course involves 3-6 treatments. Supplemental injections may be needed. Do not overfill contour deficiency. For patients with severe facial fat loss, the average treatment requires ~1 vial per cheek area per treatment.
Route of Administration: Other
Name Type Language
LACTIC ACID, L-
II  
Common Name English
L-LACTIC ACID
MI  
Common Name English
L- LACTIC ACID (+)
Common Name English
(S)-(+)-LACTIC ACID
Systematic Name English
L(+)-LACTIC ACID
Common Name English
(S)-LACTIC ACID [EP MONOGRAPH]
Common Name English
SARCOLACTICUM ACIDUM [HPUS]
Common Name English
(2S)-2-HYDROXYPROPANOIC ACID
Systematic Name English
LACTIC ACID, L- [II]
Common Name English
L-LACTIC ACID [MI]
Common Name English
(+)-LACTIC ACID
Systematic Name English
(S)-LACTIC ACID
EP  
Systematic Name English
Sarcolactic acid [WHO-DD]
Common Name English
SARCOLACTICUM ACIDUM
HPUS  
Common Name English
DEXTROROTATORY LACTIC ACID
Common Name English
SARCOLACTIC ACID
WHO-DD  
Common Name English
PARALACTIC ACID
Common Name English
L-(+)-LACTIC ACID
Common Name English
L-LACTIC ACID [JAN]
Common Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 128929
Created by admin on Fri Dec 15 15:05:58 GMT 2023 , Edited by admin on Fri Dec 15 15:05:58 GMT 2023
Code System Code Type Description
RS_ITEM_NUM
1356734
Created by admin on Fri Dec 15 15:05:58 GMT 2023 , Edited by admin on Fri Dec 15 15:05:58 GMT 2023
PRIMARY
EVMPD
SUB11686MIG
Created by admin on Fri Dec 15 15:05:58 GMT 2023 , Edited by admin on Fri Dec 15 15:05:58 GMT 2023
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FDA UNII
F9S9FFU82N
Created by admin on Fri Dec 15 15:05:58 GMT 2023 , Edited by admin on Fri Dec 15 15:05:58 GMT 2023
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EVMPD
SUB35198
Created by admin on Fri Dec 15 15:05:58 GMT 2023 , Edited by admin on Fri Dec 15 15:05:58 GMT 2023
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RXCUI
2462499
Created by admin on Fri Dec 15 15:05:58 GMT 2023 , Edited by admin on Fri Dec 15 15:05:58 GMT 2023
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NCI_THESAURUS
C61808
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DAILYMED
F9S9FFU82N
Created by admin on Fri Dec 15 15:05:58 GMT 2023 , Edited by admin on Fri Dec 15 15:05:58 GMT 2023
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EPA CompTox
DTXSID6034689
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MERCK INDEX
m6655
Created by admin on Fri Dec 15 15:05:58 GMT 2023 , Edited by admin on Fri Dec 15 15:05:58 GMT 2023
PRIMARY Merck Index
CHEBI
422
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DRUG BANK
DB14475
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PUBCHEM
107689
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SMS_ID
100000076647
Created by admin on Fri Dec 15 15:05:58 GMT 2023 , Edited by admin on Fri Dec 15 15:05:58 GMT 2023
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CAS
79-33-4
Created by admin on Fri Dec 15 15:05:58 GMT 2023 , Edited by admin on Fri Dec 15 15:05:58 GMT 2023
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ECHA (EC/EINECS)
201-196-2
Created by admin on Fri Dec 15 15:05:58 GMT 2023 , Edited by admin on Fri Dec 15 15:05:58 GMT 2023
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