D-penicillamine

Modify Date: 2024-01-02 13:06:25

D-penicillamine Structure
D-penicillamine structure
 Common Name D-penicillamine
CAS Number 52-67-5 Molecular Weight 149.211
Density 1.2±0.1 g/cm3 Boiling Point 251.8±35.0 °C at 760 mmHg
Molecular Formula C5H11NO2S Melting Point 210 °C (dec.)(lit.)
MSDS Chinese USA Flash Point 106.1±25.9 °C
Symbol GHS07
GHS07		 Signal Word Warning

 Use of D-penicillamine


Penicillamine is the most characteristic degradation product of the penicillin antibiotics. It is used as an antirheumatic and as a chelating agent in Wilson's disease.Target: OthersPenicillamine(Cuprimine, Depen) is used as an antirheumatic and as a chelating agent in Wilson's disease and is a chelating agent recommended for the removal of excess copper in patients with Wilson's disease. From in vitro studies which indicate that one atom of copper combines with two molecules of penicillamine. Penicillamine also reduces excess cystine excretion in cystinuria. The mechanism of action of penicillamine in rheumatoid arthritis is unknown although it appears to suppress disease activity. Unlike cytotoxic immunosuppressants, penicillamine markedly lowers IgM rheumatoid factor but produces no significant depression in absolute levels of serum immunoglobulins. Also unlike cytotoxic immunosuppressants which act on both, penicillamine in vitro depresses T-cell activity but not B-cell activity [1-3].

 Names

Name D-penicillamine
Synonym More Synonyms

 D-penicillamine Biological Activity

Description Penicillamine is the most characteristic degradation product of the penicillin antibiotics. It is used as an antirheumatic and as a chelating agent in Wilson's disease.Target: OthersPenicillamine(Cuprimine, Depen) is used as an antirheumatic and as a chelating agent in Wilson's disease and is a chelating agent recommended for the removal of excess copper in patients with Wilson's disease. From in vitro studies which indicate that one atom of copper combines with two molecules of penicillamine. Penicillamine also reduces excess cystine excretion in cystinuria. The mechanism of action of penicillamine in rheumatoid arthritis is unknown although it appears to suppress disease activity. Unlike cytotoxic immunosuppressants, penicillamine markedly lowers IgM rheumatoid factor but produces no significant depression in absolute levels of serum immunoglobulins. Also unlike cytotoxic immunosuppressants which act on both, penicillamine in vitro depresses T-cell activity but not B-cell activity [1-3].
Related Catalog
References

[1]. Peisach, J. and W.E. Blumberg, A mechanism for the action of penicillamine in the treatment of Wilson's disease. Mol Pharmacol, 1969. 5(2): p. 200-9.

[2]. Jaffe, I.A., K. Altman, and P. Merryman, The Antipyridoxine Effect of Penicillamine in Man. J Clin Invest, 1964. 43: p. 1869-73.

[3]. Camp, A.V., Penicillamine in the treatment of rheumatoid arthritis. Proc R Soc Med, 1977. 70(2): p. 67-9.

 Chemical & Physical Properties

Density 1.2±0.1 g/cm3
Boiling Point 251.8±35.0 °C at 760 mmHg
Melting Point 210 °C (dec.)(lit.)
Molecular Formula C5H11NO2S
Molecular Weight 149.211
Flash Point 106.1±25.9 °C
Exact Mass 149.051056
PSA 102.12000
LogP 0.93
Vapour Pressure 0.0±1.1 mmHg at 25°C
Index of Refraction 1.528
Storage condition 2~8°C
Water Solubility 11.1 g/100 mL (20 ºC)

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
YV9425000
CHEMICAL NAME :
Valine, 3-mercapto-, D-
CAS REGISTRY NUMBER :
52-67-5
LAST UPDATED :
199609
DATA ITEMS CITED :
47
MOLECULAR FORMULA :
C5-H11-N-O2-S
MOLECULAR WEIGHT :
149.23
WISWESSER LINE NOTATION :
SHX1&1&YZVQ -D

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
900 mg/kg/26W-I
TOXIC EFFECTS :
Skin and Appendages - dermatitis, other (after systemic exposure)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
650 gm/kg/81W-I
TOXIC EFFECTS :
Behavioral - muscle weakness Musculoskeletal - other changes
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
112 mg/kg/1W-I
TOXIC EFFECTS :
Blood - agranulocytosis Skin and Appendages - dermatitis, other (after systemic exposure) Nutritional and Gross Metabolic - body temperature increase
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
105 mg/kg/6W-I
TOXIC EFFECTS :
Skin and Appendages - dermatitis, other (after systemic exposure)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
400 mg/kg/4W-I
TOXIC EFFECTS :
Lungs, Thorax, or Respiration - other changes Blood - hemorrhage
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
150 mg/kg/30D-I
TOXIC EFFECTS :
Behavioral - muscle weakness Cardiac - arrhythmias (including changes in conduction) Gastrointestinal - hypermotility, diarrhea
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human
DOSE/DURATION :
21 mg/kg/D
TOXIC EFFECTS :
Kidney, Ureter, Bladder - proteinuria Blood - leukopenia Blood - thrombocytopenia
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human
DOSE/DURATION :
893 mg/kg/30W-I
TOXIC EFFECTS :
Behavioral - muscle weakness Lungs, Thorax, or Respiration - dyspnea Musculoskeletal - other changes
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - child
DOSE/DURATION :
40 mg/kg/1W-I
TOXIC EFFECTS :
Blood - leukopenia Skin and Appendages - dermatitis, other (after systemic exposure) Nutritional and Gross Metabolic - body temperature increase
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
482 mg/kg/19W-I
TOXIC EFFECTS :
Blood - thrombocytopenia Skin and Appendages - dermatitis, other (after systemic exposure)
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
6170 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
2080 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
4020 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
2 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
720 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
298 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
3810 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
3840 mg/kg
TOXIC EFFECTS :
Lungs, Thorax, or Respiration - dyspnea
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
4480 mg/kg/3W-I
TOXIC EFFECTS :
Liver - other changes Kidney, Ureter, Bladder - other changes
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
23400 mg/kg/26W-I
TOXIC EFFECTS :
Kidney, Ureter, Bladder - other changes in urine composition Blood - normocytic anemia Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
40320 mg/kg/12W-C
TOXIC EFFECTS :
Spinal Cord - other degenerative changes Autonomic Nervous System - other (direct) parasympathomimetic Nutritional and Gross Metabolic - changes in metals, not otherwise specified
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - child
DOSE/DURATION :
122 gm/kg/3Y-C
TOXIC EFFECTS :
Tumorigenic - Carcinogenic by RTECS criteria Blood - leukemia
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
2 gm/kg/4W-I
TOXIC EFFECTS :
Tumorigenic - equivocal tumorigenic agent by RTECS criteria Blood - leukemia Blood - lymphoma, including Hodgkin's disease
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Unreported
DOSE :
6480 mg/kg
SEX/DURATION :
female 1-39 week(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Specific Developmental Abnormalities - skin and skin appendages Reproductive - Specific Developmental Abnormalities - body wall
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
9130 mg/kg
SEX/DURATION :
female 1-22 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - other effects to embryo
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
1870 mg/kg
SEX/DURATION :
female 1-22 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Newborn - other neonatal measures or effects
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
41 gm/kg
SEX/DURATION :
male 60 day(s) pre-mating female 14 day(s) pre-mating - 7 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - mating performance (e.g. # sperm positive females per # females mated; # copulations per # estrus cycles) Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea) Reproductive - Fertility - other measures of fertility
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
1750 mg/kg
SEX/DURATION :
female 17-22 day(s) after conception lactating female 21 day(s) post-birth
TOXIC EFFECTS :
Reproductive - Effects on Newborn - sex ratio
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
1375 mg/kg
SEX/DURATION :
female 7-17 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
9130 mg/kg
SEX/DURATION :
female 1-22 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - skin and skin appendages Reproductive - Specific Developmental Abnormalities - musculoskeletal system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
8715 mg/kg
SEX/DURATION :
female 1-21 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - respiratory system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
5 gm/kg
SEX/DURATION :
female 15-19 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - musculoskeletal system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
20160 mg/kg
SEX/DURATION :
female 1-21 day(s) after conception lactating female 21 day(s) post-birth
TOXIC EFFECTS :
Reproductive - Effects on Newborn - weaning or lactation index (e.g., # alive at weaning per # alive at day 4) Reproductive - Effects on Newborn - other neonatal measures or effects Reproductive - Effects on Newborn - behavioral
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
10080 mg/kg
SEX/DURATION :
female 1-21 day(s) after conception lactating female 21 day(s) post-birth
TOXIC EFFECTS :
Reproductive - Effects on Newborn - other postnatal measures or effects
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
20 gm/kg
SEX/DURATION :
female 10-14 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetal death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
16 gm/kg
SEX/DURATION :
female 10-14 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
3200 mg/kg
SEX/DURATION :
female 7 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - musculoskeletal system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
4 gm/kg
SEX/DURATION :
female 7 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetal death

MUTATION DATA

TYPE OF TEST :
Sister chromatid exchange
TEST SYSTEM :
Rodent - hamster Lung
DOSE/DURATION :
1 gm/L
REFERENCE :
MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 190,197,1987 *** REVIEWS *** TOXICOLOGY REVIEW LANCAO Lancet. (7 Adam St., London WC2N 6AD, UK) V.1- 1823- Volume(issue)/page/year: 1,673,1971 TOXICOLOGY REVIEW PBPSDY Pharmacological and Biochemical Properties of Drug Substances. (American Pharmaceutical Assoc., 2215 Constitution Ave., NW, Washington, DC 20037) V.1- 1977- Volume(issue)/page/year: 2,465,1979 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X4379 No. of Facilities: 41 (estimated) No. of Industries: 2 No. of Occupations: 11 No. of Employees: 4077 (estimated) No. of Female Employees: 1600 (estimated)

 Safety Information

Symbol GHS07
GHS07
Signal Word Warning
Hazard Statements H315-H319-H335
Precautionary Statements P261-P305 + P351 + P338
Personal Protective Equipment dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes Xi,T,Xn
Risk Phrases R36/37/38
Safety Phrases S26-S36-S24/25
RIDADR NONH for all modes of transport
WGK Germany 2
RTECS YV9425000
HS Code 2930909090

 Customs

HS Code 2930909090
Summary 2930909090. other organo-sulphur compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

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 Synonyms

3,3-Dimethyl-D-cysteine,3-Mercapto-D-valine,D-(−)-2-Amino-3-mercapto-3-methylbutanoic acid
3-mercapto-L-valine
H-D-Pen-OH
3-Sulfanyl-L-valine
penicillamine
(2R)-2-amino-3-mercapto-3-methylbutanoic acid
Cuprenil
EINECS 200-148-8
Cuprimin
emtexate
Perdolat
(2S)-2-amino-3-methyl-3-sulfanylbutanoic acid
L-Penicillamine
D-β,β-Dimethylcysteine
(R)-penicillamine
Depamine
3,3-Dimethyl-D(-)-cysteine
Sufirtan
3-mercapto-D-valine
D(-)-Penicillamine
Depen
(2R)-2-amino-3-mercapto-3-methyl-butyric acid
d-valin
MFCD00064302
D-β-Mercaptovaline
usan
L-Valine, 3-mercapto-
D-PenicillaMine
Artamine
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Related Compounds: More...
D-Penicillamine
771431-20-0
D-PENICILLAMINEHCL
2219-30-9
D-Penicillamine-HCl
87457-85-0
Boc-D-Penicillamine
119222-62-7
Fmoc-D-Penicillamine
132930-71-3
S-benzyl-D-penicillamine
54536-37-7
N-formyl-D-penicillamine
13833-89-1
S-Trityl-D-penicillamine
150025-01-7
N-Acetyl-D-penicillamine
15537-71-0
Chemsrc provides D-penicillamine(CAS#:52-67-5) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of D-penicillamine are included as well.>> amp version: D-penicillamine

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