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Glucosamine(CAS No. 3416-24-8)

Glucosamine C6H13NO5 (cas 3416-24-8) Molecular Structure

3416-24-8 Structure

Identification and Related Records

【CAS Registry number】
Glucosamine, D-
【Molecular Formula】
C6H13NO5 (Products with the same molecular formula)
【Molecular Weight】
【Canonical SMILES】
【Isomers smiles】

Chemical and Physical Properties

1.563 g/cm3
【Melting Point】
88 deg C
【Boiling Point】
449.9 °C at 760 mmHg
【Flash Point】
225.9 °C
Soluble in water
Soluble in water
【Computed Properties】
Molecular Weight:179.17112 [g/mol]
Molecular Formula:C6H13NO5
H-Bond Donor:5
H-Bond Acceptor:6
Rotatable Bond Count:1
Exact Mass:179.079373
MonoIsotopic Mass:179.079373
Topological Polar Surface Area:116
Heavy Atom Count:12
Formal Charge:0
Isotope Atom Count:0
Defined Atom Stereocenter Count:5
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:5
Feature 3D Donor Count:5
Feature 3D Cation Count:1
Feature 3D Ring Count:1
Effective Rotor Count:2.2
Conformer Sampling RMSD:0.6
CID Conformer Count:6

Safety and Handling

The three forms of glucosamine available commercially are glucosamine hydrochloride, glucosamine sulfate and N-acetyl glucosamine.
【Octanol/Water Partition Coefficient】
log Kow = -4.2 (est)
【Disposal Methods】
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

Found in chitin, in mucoproteins, and in mucopolysaccharides.

Biomedical Effects and Toxicity

【Therapeutic Uses】
Glucosamine and chondroitin sulfate are used to treat osteoarthritis. The multicenter, double-blind, placebo- and celecoxib-controlled Glucosamine/chondroitin Arthritis Intervention Trial (GAIT) evaluated their efficacy and safety as a treatment for knee pain from osteoarthritis. 1583 patients with symptomatic knee osteoarthritis /were randomly assigned/ to receive 1500 mg of glucosamine daily, 1200 mg of chondroitin sulfate daily, both glucosamine and chondroitin sulfate, 200 mg of celecoxib daily, or placebo for 24 weeks. Up to 4000 mg of acetaminophen daily was allowed as rescue analgesia. Assignment was stratified according to the severity of knee pain (mild [N=1229] vs. moderate to severe [N=354]). The primary outcome measure was a 20 percent decrease in knee pain from baseline to week 24. The mean age of the patients was 59 years, and 64 percent were women. Overall, glucosamine and chondroitin sulfate were not significantly better than placebo in reducing knee pain by 20 percent. As compared with the rate of response to placebo (60.1 percent), the rate of response to glucosamine was 3.9 percentage points higher (P=0.30), the rate of response to chondroitin sulfate was 5.3 percentage points higher (P=0.17), and the rate of response to combined treatment was 6.5 percentage points higher (P=0.09). The rate of response in the celecoxib control group was 10.0 percentage points higher than that in the placebo control group (P=0.008). For patients with moderate-to-severe pain at baseline, the rate of response was significantly higher with combined therapy than with placebo (79.2 percent vs. 54.3 percent, P=0.002). Adverse events were mild, infrequent, and evenly distributed among the groups. Glucosamine and chondroitin sulfate alone or in combination did not reduce pain effectively in the overall group of patients with osteoarthritis of the knee. Exploratory analyses suggest that the combination of glucosamine and chondroitin sulfate may be effective in the subgroup of patients with moderate-to-severe knee pain. [Clegg DO et al; New Eng J Med 354: 795-808 (2006)]
【Biomedical Effects and Toxicity】
Information on the absorption and serum pharmacokinetics for dietary glucosamine is very limited, and in some case, the available data are contradictory. For example, in one series of studies, (14)C-glucosamine was given orally to rats, dogs, and humans, and in all cases, the radiolabel was described as "efficiently" absorbed, reaching a plasma peak after about 4 hours. A high percentage of the radiolabel (about 35%) was excreted in the urine, and a similar amount was last in expired air. On the other hand, the laboratory that conducted this experiment was unable to detect chemical amounts of glucosamine in human serum after a single oral dose at 100 mg/kg (five times the clinical dose) using a chromatographic assay with a limit of detection of about 14 uM. This suggests that the bioavailable glucosamine in human serum after the normal recommended dosage (20 mg/kg) is well below 10 uM.
About 90% of glucosamine administered orally as a glucosamine salt get absorbed from the small intestine, and from there it is transported via the portal circulation to the liver. It appears that a significant fraction of the ingested glucosamine is catabolized by first-pass metabolism in the liver. Free glucosamine is not detected in the serum after oral intake, and it si not presently known how much of an ingested dose is taken up in the joints in humans. Some uptake in the articular cartilage is seen in animal studies.
Twelve healthy volunteers received three consecutive once-daily oral administrations of glucosamine sulfate soluble powder at the doses of 750, 1,500, and 3,000 mg, in an open, randomised, cross-over fashion. Glucosamine was determined in plasma collected up to 48 hr after the last dose. ... Endogenous plasma levels of glucosamine were detected (10.4-204 ng/ml, with low intra-subject variability). Glucosamine was rapidly absorbed after oral administration and its pharmacokinetics were linear in the dose range 750-1,500 mg, but not at 3,000 mg, where the plasma concentration-time profiles were less than expected based on dose-proportionality. Plasma levels increased over 30-folds from baseline and peaked at about 10 microM with the standard 1,500 mg once-daily dosage. Glucosamine distributed to extravascular compartments and its plasma concentrations were still above baseline up to the last collection time. [Persiani S et al; Osteoarthritis Cartilage 13 (12): 1041-9 (2005)] PubMed Abstract
Eighteen subjects with osteoarthritis were given 1,500 mg of commercial glucosamine sulphate after an overnight fast, and serum was then obtained at baseline and every 15-30 minutes over 3 hours, and additionally, from two subjects at 5 and 8 hours. Urine samples were collected at baseline and 3 hours after ingestion from three subjects. Baseline glucosamine was below the detection limit of 0.5 umol/L for all subjects, but after ingestion, glucosamine was detected in 17/18 subjects, beginning to rise at 30-45 minutes to a maximum at 90-180 minutes, with a range of 1.9-11.5 umol/L (0.34-2 ug/ml). [Bittee BA et al; Ann Rheum Dis 65 (2): 222-6 (2006)] PubMed Abstract
The purpose of this study was to determine if glucosamine (GL) hydrochloride (FCHG49) and low molecular weight (LMW) chondroitin sulfate (CS) (TRH122) are absorbed after oral administration to horses. The bioavailability of LMWCS was evaluated by quantifying the total disaccharides found in the plasma following chondroitinase ABC digestion. Two separate studies were conducted. In study 1, ten adult horses received the following four treatments in a randomized crossover fashion: (1) i.v. LMWCS (3 g of 8 kDa), (2) p.o. LMWCS (3 g of 8 kDa), (3) i.v. LMWCS (3 g of 16.9 kDa) and (4) p.o. LMWCS (3 g of 16.9 kDa). Each group received 9 g GL with LMWCS. In a second study, each horse (n=2) was randomly assigned to receive either i.v. administration of GL HCl (9 g) or p.o. administration of GL HCl (125 mg/kg). Blood samples were collected, assayed and pharmacokinetic parameters were determined. GL was absorbed after oral dosing with a mean C(max) of 10.6 (6.9) ug/ml and a mean T(max) of 2.0 (0.7) hr. The extent of absorption of LMWCS after dosing with both the 8.0 and 16.9 kDa provides evidence that LMWCS is absorbed orally. C(max) and AUC were higher (pPubMed Abstract
The purpose of this study was to determine the oral bioavailability and pharmacokinetics of a glucosamine and the disaccharides of chondroitin sulfate after single and multiple-dosing of a glucosamine/chondroitin sulfate combination (Cosamin, Cosequin). Male beagle dogs (n = 8, 12 kg) received the following treatments: (1) IV glucosamine (500 mg)/chondroitin sulfate (400 mg), (2) p.o. glucosamine (1500 mg)/chondroitin sulfate (1200 mg), (3) p.o. glucosamine (2000 mg)/chondroitin sulfate (1600 mg), (4) p.o. glucosamine (1500 mg)/chondroitin sulfate (1200 mg) QD for days 1-7 and p.o. glucosamine (3000 mg)/chondroitin sulfate (2400 mg) from days 8 to 14. Blood samples were collected over 24 hr and glucosamine and the disaccharides of chondroitin sulfate were determined. Pharmacokinetic analysis was performed on glucosamine and total chondroitin sulfate disaccharides and parameters were compared across treatments using ANOVA with post hoc analysis. After the IV administration, glucosamine declined rapidly in a bi-exponential fashion with a mean (+ or - S.D.) elimination t(1/2) of 0.52 (0.25) hr. Glucosamine absorption was relatively fast (C(max) = 8.95 ug/ml, and T(max) 1.5 h after 1500 mg dose) and the mean bioavailability of glucosamine after single dosing was approximately 12%. The extent of absorption of chondroitin sulfate as indicated by the mean C(max) (21.5 ug/ml) and mean AUC (187 ug/ml hr) of total disaccharides after dosing (1600 mg) provides evidence that chondroitin sulfate is absorbed orally. The bioavailability of chondroitin sulfate ranged from 4.8 to 5.0% after single dosing and 200-278% upon multiple dosing. The results of this study show that both glucosamine and chondroitin sulfate (measured as total disaccharides) are bioavailable after oral dosing. In addition, the low molecular weight chondroitin sulfate used in this study displays significant accumulation upon multiple dosing. [Adebowale A et al; Biopharm Drug Dispos 23 (6): 217-25 (2002)] PubMed Abstract
The pharmacokinetics of glucosamine sulfate was investigated in 6 healthy male volunteers (2 per administration route) using (14)C uniformly labelled glucosamine sulfate and administering it in single dose by intravenous (i.v.), intramuscular (i.m.) or oral route. The results show that after i.v. administration the radioactivity due to glucosamine appears in plasma and is rapidly eliminated, with an initial t1/2 of 0.28 hr. 1-2 hr after administration the radioactivity due to glucosamine disappears almost completely and is replaced by a radioactivity originating from plasma proteins, in which glucosamine or its metabolites are incorporated. This radioactivity reaches a peak after 8-10 hr and then declines with a t1/2 of 70 hr. About 28% of the administered radioactivity is recovered in the urine of the 120 hr following the administration and less than 1% is recovered in the feces. After i.m. administration similar pharmacokinetic patterns are observed. After oral administration a proportion close to 90% of glucosamine sulfate is absorbed. Free glucosamine is not detectable in plasma. The radioactivity incorporated in the plasma proteins follows pharmacokinetic patterns which are similar to those after i.v. or i.m. administration, but its concentration in plasma is about 5 times smaller than that after parenteral administration. The AUC after oral administration is 26% of that after i.v., or i.m. administration. The smaller plasma levels of radioactivity after oral administration are probably due to a first pass effect in the liver which metabolizes a notable proportion of glucosamine into smaller molecules and ultimately to CO2, water and urea. [Setnikar I et al; Arzneimittelforschung 43 (10): 1109-13 (1993)] PubMed Abstract

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that glucosamine is expected to have very high mobility in soil(SRC). The pKa of glucosamine is 7.58(3), indicating that this compound will partially exist in cation form in the environment and cations generally absorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization of the neutral form of glucosamine from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 7.7X10-16 atm-cu m/mole(SRC), using a fragment constant estimation method(5). Volatilization of the cation from moist soil surfaces will not occur as ionic species do not volatilize. Glucosamine is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 9.0X10-8 mm Hg(SRC), determined from a fragment constant method(6). Glucosamine is expected to biodegrade fairly rapidly in aerobic soil environments based on a grab sample study using two different soils where 36 and 56% mineralization and 65 and 70% mineralization were reported after 1 and 8 weeks, respectively(7).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that glucosamine is not expected to adsorb to suspended solids and sediment(SRC). However, glucosamine will exist partially in the cation form at pH values of 5 to 9 based on a pKa of 7.58(5) and cations generally adsorb more strongly to organic carbon and clay than their neutral counterparts(6). Volatilization from water surfaces is not expected(3) for the neutral species based upon an estimated Henry's Law constant of 7.7X10-16 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Volatilization of the cation from water surfaces is not expected to occur as ionic species do not volatilize. According to a classification scheme(7), an estimated BCF of 3(SRC), from an estimated log Kow of -4.2(8) and a regression-derived equation(9), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Glucosamine is expected to biodegrade fairly rapidly in aerobic water based on a soil grab sample study using two different soils where 36 and 56% mineralization and 65 and 70% mineralization were reported after 1 and 8 weeks, respectively(10).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), glucosamine, which has an estimated vapor pressure of 9.0X10-8 mm Hg at 25 deg C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase glucosamine may be removed from the air by wet or dry deposition(SRC). Glucosamine does not contain a chromophore that absorbs at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight(3).

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