Hydroxyproline
Identification
- Generic Name
- Hydroxyproline
- DrugBank Accession Number
- DB08847
- Background
Hydroxyproline is a neutral heterocyclic protein amino acid. It is found in collagen and as such it is common in many gelatin products. Hydroxyproline is mostly used as a diagnostic marker of bone turnover and liver fibrosis. Therapeutically, hydroxyproline is being studied as an an experimental medicine but is approved in France as a combination topical gel product called Cicactive for small, superficial wounds.
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 131.1299
Monoisotopic: 131.058243159 - Chemical Formula
- C5H9NO3
- Synonyms
- trans-4-Hydroxy-L-proline
- trans-L-Hydroxyproline
Pharmacology
- Indication
Used in France as a combination product for the treatment of small, superficial wounds.
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- Pharmacodynamics
Hydroxyproline as well as proline and glycine are the major components of collagen. Collagen is on one of the main building blocks of connective tissue such as skin, bone, and cartilage. Thus when these tissues are damaged, hydroxyproline is necessary for repair of the damaged area.
- Mechanism of action
- Not Available
- Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Isa Knox Wrinkle Decline Double Effect Rf3 Wrinkle Cream 0.525 mL/100mL Topical Lg Household & Health Care Ltd. 2010-05-20 2011-03-01 US Isa Knox Wrinkle Decline Double Effect Rf3 Wrinkle Eye Filler Cream 0.525 mL/100mL Topical Lg Household & Health Care Ltd. 2010-05-14 2011-03-01 US O Hui Wrinkle Science Deep Wrinkle Treatment Cream 0.5 mL/100mL Topical Lg Household & Health Care Ltd. 2010-04-30 2011-06-01 US O Hui Wrinkle Science Wrinkle Repair Cream 0.5 1/100mL Topical Lg Household & Health Care Ltd. 2010-04-16 Not applicable US Ohui Skin Science Age Recovery Cell Lab Cream 0.5 mL/100mL Topical Lg Household & Health Care Ltd. 2011-01-20 2012-04-01 US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Ageless Foundation 23 Hydroxyproline (0.53 mL/100mL) + Diacetyl benzoyl lathyrol (0.1 mL/100mL) + Dimethicone (0.34 mL/100mL) + Distearyldimonium chloride (0.3 mL/100mL) + Octinoxate (1.5 mL/100mL) + Titanium dioxide (8.24 mL/100mL) Liquid Topical Lg Household & Health Care Ltd. 2010-10-22 2011-10-22 US Cathycat Chewy CREAM FOUNDATION SPF23 PA WHITENING ANTI WRINKLE 21 Hydroxyproline (0.5 g/100g) + Arbutin (2 g/100g) + Octinoxate (1.5 g/100g) + Titanium dioxide (8.2062 g/100g) Liquid Topical Lg Household & Health Care Ltd. 2011-04-15 2012-04-15 US Cathycat Chewy CREAM FOUNDATION SPF23 PA WHITENING ANTI WRINKLE 23 Hydroxyproline (0.5 g/100g) + Arbutin (2 g/100g) + Octinoxate (1.5 g/100g) + Titanium dioxide (8.2062 g/100g) Liquid Topical Lg Household & Health Care Ltd. 2011-04-15 2012-04-15 US Gongjinhyang Mi Luxury Base Hydroxyproline (0.057 mL/100mL) + Honey (0.01 mL/100mL) + Titanium dioxide (0.057 mL/100mL) Cream Topical Lg Household & Health Care Ltd. 2010-04-09 2011-04-09 US Gongjinhyang Mi Luxury Foundation 1 Hydroxyproline (0.53 mL/100mL) + Octinoxate (1 mL/100mL) Cream Topical Lg Household & Health Care Ltd. 2010-03-30 2011-03-30 US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Isa Knox Tervina Repair Foundation Bb Hydroxyproline (0.5 mL/100mL) + Atractylodes lancea root oil (0.05 mL/100mL) + Octinoxate (3 mL/100mL) + Titanium dioxide (1 mL/100mL) Liquid Topical Lg Household & Health Care Ltd. 2011-07-01 2012-04-01 US Isa Knox Wrinkle Decline Double Effect Rf3 Wrinkle Hydroxyproline (0.525 mL/100mL) Cream Topical Lg Household & Health Care Ltd. 2010-05-20 2011-03-01 US Isa Knox Wrinkle Decline Double Effect Rf3 Wrinkle Eye Filler Hydroxyproline (0.525 mL/100mL) Cream Topical Lg Household & Health Care Ltd. 2010-05-14 2011-03-01 US O Hui Wrinkle Science Deep Wrinkle Treatment Hydroxyproline (0.5 mL/100mL) Cream Topical Lg Household & Health Care Ltd. 2010-04-30 2011-06-01 US O Hui Wrinkle Science Wrinkle Repair Hydroxyproline (0.5 1/100mL) Cream Topical Lg Household & Health Care Ltd. 2010-04-16 Not applicable US
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as proline and derivatives. These are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Carboxylic acids and derivatives
- Sub Class
- Amino acids, peptides, and analogues
- Direct Parent
- Proline and derivatives
- Alternative Parents
- L-alpha-amino acids / Pyrrolidine carboxylic acids / Secondary alcohols / Amino acids / 1,2-aminoalcohols / Monocarboxylic acids and derivatives / Dialkylamines / Carboxylic acids / Azacyclic compounds / Organopnictogen compounds show 3 more
- Substituents
- 1,2-aminoalcohol / Alcohol / Aliphatic heteromonocyclic compound / Alpha-amino acid / Amine / Amino acid / Azacycle / Carbonyl group / Carboxylic acid / Hydrocarbon derivative show 16 more
- Molecular Framework
- Aliphatic heteromonocyclic compounds
- External Descriptors
- 4-hydroxyproline (CHEBI:18095) / Other amino acids (C01157)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- RMB44WO89X
- CAS number
- 51-35-4
- InChI Key
- PMMYEEVYMWASQN-DMTCNVIQSA-N
- InChI
- InChI=1S/C5H9NO3/c7-3-1-4(5(8)9)6-2-3/h3-4,6-7H,1-2H2,(H,8,9)/t3-,4+/m1/s1
- IUPAC Name
- (2S,4R)-4-hydroxypyrrolidine-2-carboxylic acid
- SMILES
- O[C@H]1CN[C@@H](C1)C(O)=O
References
- Synthesis Reference
Adams, Elijah; Goldstone, Alfred. Hydroxyproline metabolism. II. Enzymic preparation and properties of D1-pyrroline-3-hydroxy-5-carboxylic acid. Journal of Biological Chemistry (1960), 235 3492-8.
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0000725
- KEGG Compound
- C01157
- PubChem Compound
- 5810
- PubChem Substance
- 175427120
- ChemSpider
- 5605
- BindingDB
- 50357233
- 1311548
- ChEBI
- 18095
- ChEMBL
- CHEMBL352418
- ZINC
- ZINC000000901791
- PDBe Ligand
- HYP
- Wikipedia
- Hydroxyproline
- PDB Entries
- 1ag7 / 1as5 / 1av3 / 1bdk / 1bkv / 1cag / 1cgd / 1d7t / 1dfy / 1dfz … show 345 more
- MSDS
- Download (72.1 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 1, 2 Completed Treatment Hyperoxaluria 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Cream Topical Cream Topical 0.5 mL/100mL Cream Topical 0.5 1/100mL Emulsion Topical 0.5 mL/100mL Cream Topical 0.51 1/100mL Liquid Topical Cream Topical 0.525 mL/100mL - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 274°C From The Merck Index monographs. boiling point (°C) Decomposes From MSDS. water solubility Soluble in water at 0, 25, 50, and 60 °C From The Merck Index monographs. pKa pK1′ 1.82 and pK2′ 9.65 From The Merck Index monographs. - Predicted Properties
Property Value Source Water Solubility 492.0 mg/mL ALOGPS logP -3.3 ALOGPS logP -3.7 Chemaxon logS 0.57 ALOGPS pKa (Strongest Acidic) 1.64 Chemaxon pKa (Strongest Basic) 10.62 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 69.56 Å2 Chemaxon Rotatable Bond Count 1 Chemaxon Refractivity 29.38 m3·mol-1 Chemaxon Polarizability 12.29 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9652 Blood Brain Barrier + 0.6522 Caco-2 permeable - 0.7144 P-glycoprotein substrate Non-substrate 0.546 P-glycoprotein inhibitor I Non-inhibitor 0.9789 P-glycoprotein inhibitor II Non-inhibitor 0.987 Renal organic cation transporter Non-inhibitor 0.856 CYP450 2C9 substrate Non-substrate 0.8242 CYP450 2D6 substrate Non-substrate 0.7501 CYP450 3A4 substrate Non-substrate 0.6878 CYP450 1A2 substrate Non-inhibitor 0.9332 CYP450 2C9 inhibitor Non-inhibitor 0.9619 CYP450 2D6 inhibitor Non-inhibitor 0.9367 CYP450 2C19 inhibitor Non-inhibitor 0.9623 CYP450 3A4 inhibitor Non-inhibitor 1.0 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9913 Ames test Non AMES toxic 0.9149 Carcinogenicity Non-carcinogens 0.964 Biodegradation Ready biodegradable 0.9178 Rat acute toxicity 2.1441 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9682 hERG inhibition (predictor II) Non-inhibitor 0.9178
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 123.0785 predictedDarkChem Lite v0.1.0 [M-H]- 123.0768 predictedDarkChem Lite v0.1.0 [M-H]- 123.1028 predictedDarkChem Lite v0.1.0 [M-H]- 121.71372 predictedDeepCCS 1.0 (2019) [M+H]+ 124.2009 predictedDarkChem Lite v0.1.0 [M+H]+ 126.8448467 predictedDarkChem Standard v0.1.0 [M+H]+ 123.4132 predictedDarkChem Lite v0.1.0 [M+H]+ 125.39543 predictedDeepCCS 1.0 (2019) [M+Na]+ 123.6804 predictedDarkChem Lite v0.1.0 [M+Na]+ 122.2965 predictedDarkChem Lite v0.1.0 [M+Na]+ 123.2415 predictedDarkChem Lite v0.1.0 [M+Na]+ 134.5223 predictedDeepCCS 1.0 (2019)
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- L-proline transmembrane transporter activity
- Specific Function
- Neutral amino acid/proton symporter. Has a pH-dependent electrogenic transport activity for small amino acids such as glycine, alanine and proline. Besides small apolar L-amino acids, it also recog...
- Gene Name
- SLC36A1
- Uniprot ID
- Q7Z2H8
- Uniprot Name
- Proton-coupled amino acid transporter 1
- Molecular Weight
- 53075.045 Da
References
- Metzner L, Kalbitz J, Brandsch M: Transport of pharmacologically active proline derivatives by the human proton-coupled amino acid transporter hPAT1. J Pharmacol Exp Ther. 2004 Apr;309(1):28-35. Epub 2004 Jan 12. [Article]
Drug created at March 02, 2013 01:29 / Updated at June 12, 2020 16:52