Captopril

Modify Date: 2019-06-10 11:39:17

Captopril Structure
Captopril structure
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Common Name Captopril
CAS Number 62571-86-2 Molecular Weight 217.285
Density 1.3±0.1 g/cm3 Boiling Point 427.0±40.0 °C at 760 mmHg
Molecular Formula C9H15NO3S Melting Point 104-108 °C(lit.)
MSDS Chinese USA Flash Point 212.1±27.3 °C
Symbol GHS07 GHS08
GHS07, GHS08
Signal Word Warning

 Use of Captopril


Captopril is a potent, competitive inhibitor of angiotensin-converting enzyme (ACE).Target: ACECaptopril has been shown to have similar morbidity and mortality benefits to those of diuretics and beta-blockers in hypertensive patients. Captopril has been shown to delay the progression of diabetic nephropathy, and enalapril and lisinopril prevent the development of nephropathy in normoalbuminuric patients with diabetes [1]. an equimolar ratio of the cis and trans states of captopril exists in solution and that the enzyme selects only the trans state of the inhibitor that presents architectural and stereoelectronic complementarity with its substrate binding groove [2].

 Names

Name captopril
Synonym More Synonyms

 Captopril Biological Activity

Description Captopril is a potent, competitive inhibitor of angiotensin-converting enzyme (ACE).Target: ACECaptopril has been shown to have similar morbidity and mortality benefits to those of diuretics and beta-blockers in hypertensive patients. Captopril has been shown to delay the progression of diabetic nephropathy, and enalapril and lisinopril prevent the development of nephropathy in normoalbuminuric patients with diabetes [1]. an equimolar ratio of the cis and trans states of captopril exists in solution and that the enzyme selects only the trans state of the inhibitor that presents architectural and stereoelectronic complementarity with its substrate binding groove [2].
Related Catalog
Solvent
In Vitro:

10 mM in DMSO

Solubility
1 mM 4.6021 mL 23.0107 mL 46.0214 mL
5 mM 0.9204 mL 4.6021 mL 9.2043 mL
10 mM 0.4602 mL 2.3011 mL 4.6021 mL
Storage
Powder -20°C 3 years
  4°C 2 years
In solvent -80°C 6 months
  -20°C 1 month
Shipping Room temperature in continental US; may vary elsewhere
SMILES O=C(O)[C@H]1N(C([C@H](C)CS)=O)CCC1
References

[1]. Tzakos, A.G., et al., The molecular basis for the selection of captopril cis and trans conformations by angiotensin I converting enzyme. Bioorg Med Chem Lett, 2006. 16(19): p. 5084-7.

[2]. Song, J.C. and C.M. White, Clinical pharmacokinetics and selective pharmacodynamics of new angiotensin converting enzyme inhibitors: an update. Clin Pharmacokinet, 2002. 41(3): p. 207-24.

Related Molecules Angiotensin I/II (1-7) | Enalapril maleate | Perindopril erbumine | Lisinopril diydrate | Phosphoramidon disodium salt | Trandolapril | Fosinopril sodium | Quinapril hydrochloride | Ramipril | Cilazapril (monohydrate) | Enalaprilat Dihydrate | omapatrilat | Temocapril (hydrochloride) | Hemorphin-7 | Moexipril (hydrochloride)
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SDS |COA |HNMR |LCMS

*The above documents are provided by Medchemexpress and are for scientific research only.

 Chemical & Physical Properties

Density 1.3±0.1 g/cm3
Boiling Point 427.0±40.0 °C at 760 mmHg
Melting Point 104-108 °C(lit.)
Molecular Formula C9H15NO3S
Molecular Weight 217.285
Flash Point 212.1±27.3 °C
Exact Mass 217.077271
PSA 96.41000
LogP 0.27
Vapour Pressure 0.0±2.2 mmHg at 25°C
Index of Refraction 1.551
Water Solubility soluble

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
UY0550000
CHEMICAL NAME :
1-Pyrrolidinecarboxylic acid, 1-(D-3-mercapto-2-methyl-1-propionyl)-, L-(S,S)-
CAS REGISTRY NUMBER :
62571-86-2
LAST UPDATED :
199609
DATA ITEMS CITED :
33
MOLECULAR FORMULA :
C9-H15-N-O3-S
MOLECULAR WEIGHT :
217.31
WISWESSER LINE NOTATION :
T5NTJ AVY1&1SH BVQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
10 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Vascular - BP lowering not characterized in autonomic section
REFERENCE :
AEMED3 Annals of Emergency Medicine. (American College of Emergency Physicians, 1125 Executive Circle, Irving, TX 75038) Volume(issue)/page/year: 20,1125,1991
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
16 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
JTCTDW Journal of Toxicology, Clinical Toxicology. (Marcel Dekker, 270 Madison Ave., New York, NY 10016) V.19- 1982- Volume(issue)/page/year: 28,379,1990
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
4 mg/kg/8D-I
TOXIC EFFECTS :
Behavioral - toxic psychosis
REFERENCE :
AJPSAO American Journal of Psychiatry. (American Psychiatric Assoc., Circulation Dept., 1400 K St., NW, Washington, DC 20005) V.78- 1921- Volume(issue)/page/year: 142,270,1985
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
239 mg/kg/6W-I
TOXIC EFFECTS :
Sense Organs and Special Senses (Taste) - change in function Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis) Blood - normocytic anemia
REFERENCE :
AJMEAZ American Journal of Medicine. (Technical Pub., 875 Third Ave., New York, NY 10022) V.1- 1946- Volume(issue)/page/year: 71,493,1981
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
2500 ug/kg/3D-I
TOXIC EFFECTS :
Kidney, Ureter, Bladder - urine volume decreased Kidney, Ureter, Bladder - other changes
REFERENCE :
PGMJAO Postgraduate Medical Journal. (Blackwell Scientific Pub. Ltd., POB 88, Oxford, UK) V.1- 1925- Volume(issue)/page/year: 60,561,1984
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
2679 ug/kg/5D-I
TOXIC EFFECTS :
Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis)
REFERENCE :
IJMDAI Israel Journal of Medical Sciences. (POB 1435, Jerusalem 91013, Israel) V.1- 1965- Volume(issue)/page/year: 21,892,1985
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
7143 ug/kg/2D-I
TOXIC EFFECTS :
Skin and Appendages - dermatitis, other (after systemic exposure)
REFERENCE :
BMJOAE British Medical Journal. (British Medical Assoc., BMA House, Tavistock Sq., London WC1H 9JR, UK) V.1- 1857- Volume(issue)/page/year: 294,91,1987
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
12500 ug/kg/25D-I
TOXIC EFFECTS :
Blood - other hemolysis with or without anemia
REFERENCE :
CMAJAX Canadian Medical Association Journal. (Canadian Medical Assoc., POB 8650, Ottawa, ON K1G 0G8, Canada) V.1- 1911- Volume(issue)/page/year: 129,525,1983
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
14 mg/kg/2W-I
TOXIC EFFECTS :
Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis) Biochemical - Metabolism (Intermediary) - other
REFERENCE :
AIMEAS Annals of Internal Medicine. (American College of Physicians, 4200 Pine St., Philadelphia, PA 19104) V.1- 1927- Volume(issue)/page/year: 104,126,1986
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
1500 ug/kg/7W
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Vascular - BP lowering not characterized in autonomic section Lungs, Thorax, or Respiration - dyspnea
REFERENCE :
AIMEAS Annals of Internal Medicine. (American College of Physicians, 4200 Pine St., Philadelphia, PA 19104) V.1- 1927- Volume(issue)/page/year: 94,58,1981
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
10 mg/kg/10D-I
TOXIC EFFECTS :
Skin and Appendages - dermatitis, other (after systemic exposure)
REFERENCE :
BMJOAE British Medical Journal. (British Medical Assoc., BMA House, Tavistock Sq., London WC1H 9JR, UK) V.1- 1857- Volume(issue)/page/year: 294,91,1987
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
87 mg/kg/18W-I
TOXIC EFFECTS :
Kidney, Ureter, Bladder - changes primarily in glomeruli Kidney, Ureter, Bladder - proteinuria Kidney, Ureter, Bladder - hematuria
REFERENCE :
AIMEAS Annals of Internal Medicine. (American College of Physicians, 4200 Pine St., Philadelphia, PA 19104) V.1- 1927- Volume(issue)/page/year: 112,550,1990
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
2680 ug/kg/5D-I
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Nutritional and Gross Metabolic - changes in potassium
REFERENCE :
SMJOAV Southern Medical Journal. (Southern Medical Assoc., POB 2446, Birmingham, AL 35205) V.1- 1908- Volume(issue)/page/year: 86,1269,1993
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
4245 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 14,297,1983
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>600 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
YAKUD5 Gekkan Yakuji. Pharmaceuticals Monthly. (Yakugyo Jihosha, Inaoka Bldg., 2-36 Jinbo-cho, Kanda, Chiyoda-ku, Tokyo 101, Japan) V.1- 1959- Volume(issue)/page/year: 24,2439,1982
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
554 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 14,297,1983
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
2500 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
PCJOAU Pharmaceutical Chemistry Journal (English Translation). Translation of KHFZAN. (Plenum Pub. Corp., 233 Spring St., New York, NY 10013) No.1- 1967- Volume(issue)/page/year: 22,212,1988
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>2400 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
YAKUD5 Gekkan Yakuji. Pharmaceuticals Monthly. (Yakugyo Jihosha, Inaoka Bldg., 2-36 Jinbo-cho, Kanda, Chiyoda-ku, Tokyo 101, Japan) V.1- 1959- Volume(issue)/page/year: 24,2439,1982
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
663 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 14,297,1983
TYPE OF TEST :
LD - Lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
>600 mg/kg
TOXIC EFFECTS :
Gastrointestinal - nausea or vomiting
REFERENCE :
44XQA7 "Captopril and Hypertension, Collection of Papers presented at a Symposium, Princeton, N.J., 1979?," Case, David B., et al. eds., New York, Plenum Publishing, 1980 Volume(issue)/page/year: -,137,1980
TYPE OF TEST :
LD - Lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Primate - monkey
DOSE/DURATION :
>1500 mg/kg
TOXIC EFFECTS :
Gastrointestinal - nausea or vomiting
REFERENCE :
44XQA7 "Captopril and Hypertension, Collection of Papers presented at a Symposium, Princeton, N.J., 1979?," Case, David B., et al. eds., New York, Plenum Publishing, 1980 Volume(issue)/page/year: -,137,1980 ** OTHER MULTIPLE DOSE TOXICITY DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
45 gm/kg/13W-I
TOXIC EFFECTS :
Kidney, Ureter, Bladder - changes in bladder weight Blood - pigmented or nucleated red blood cells Blood - changes in erythrocyte (RBC) count
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 45,15,1995
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
3 gm/kg/30D-I
TOXIC EFFECTS :
Cardiac - changes in heart weight Liver - changes in liver weight Blood - changes in other cell count (unspecified)
REFERENCE :
JTSCDR Journal of Toxicological Sciences. (Japanese Soc. of Toxicological Sciences, 4th Floor, Gakkai Center Bldg., 4-16, Yayoi 2-chome, Bunkyo-ku, Tokyo 113, Japan) V.1- 1976- Volume(issue)/page/year: 6(Suppl 2),189,1981
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
36500 mg/kg/1Y-C
TOXIC EFFECTS :
Cardiac - changes in heart weight Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Blood - changes in erythrocyte (RBC) count
REFERENCE :
JTSCDR Journal of Toxicological Sciences. (Japanese Soc. of Toxicological Sciences, 4th Floor, Gakkai Center Bldg., 4-16, Yayoi 2-chome, Bunkyo-ku, Tokyo 113, Japan) V.1- 1976- Volume(issue)/page/year: 6(Suppl 2),215,1981
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
9100 mg/kg/91D-I
TOXIC EFFECTS :
Kidney, Ureter, Bladder - other changes Skin and Appendages - dermatitis, other (after systemic exposure)
REFERENCE :
JTSCDR Journal of Toxicological Sciences. (Japanese Soc. of Toxicological Sciences, 4th Floor, Gakkai Center Bldg., 4-16, Yayoi 2-chome, Bunkyo-ku, Tokyo 113, Japan) V.1- 1976- Volume(issue)/page/year: 6(Suppl 2),247,1981
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Primate - monkey
DOSE/DURATION :
6300 mg/kg/28D-I
TOXIC EFFECTS :
Blood - other changes Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - other Enzymes
REFERENCE :
44XQA7 "Captopril and Hypertension, Collection of Papers presented at a Symposium, Princeton, N.J., 1979?," Case, David B., et al. eds., New York, Plenum Publishing, 1980 Volume(issue)/page/year: -,137,1980 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
228 mg/kg
SEX/DURATION :
male 43 week(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - breast development
REFERENCE :
BMJOAE British Medical Journal. (British Medical Assoc., BMA House, Tavistock Sq., London WC1H 9JR, UK) V.1- 1857- Volume(issue)/page/year: 296,1262,1988
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
48 gm/kg
SEX/DURATION :
male 30 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - testes, epididymis, sperm duct Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland, accessory glands
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 13,7041,1985
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
100 mg/kg
SEX/DURATION :
female 6-15 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea) 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)
REFERENCE :
RCOCB8 Research Communications in Chemical Pathology and Pharmacology. (PJD Pub. Ltd., P.O. Box 966, Westbury, NY 11590) V.1- 1970- Volume(issue)/page/year: 73,221,1991
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
100 mg/kg
SEX/DURATION :
female 6-15 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - musculoskeletal system
REFERENCE :
RCOCB8 Research Communications in Chemical Pathology and Pharmacology. (PJD Pub. Ltd., P.O. Box 966, Westbury, NY 11590) V.1- 1970- Volume(issue)/page/year: 73,221,1991
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
40 mg/kg
SEX/DURATION :
female 15-30 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetal death
REFERENCE :
PSEBAA Proceedings of the Society for Experimental Biology and Medicine. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1903/04- Volume(issue)/page/year: 170,378,1982
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
8250 ug/kg
SEX/DURATION :
female 24-28 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - other measures of fertility Reproductive - Effects on Embryo or Fetus - fetal death
REFERENCE :
LANCAO Lancet. (7 Adam St., London WC2N 6AD, UK) V.1- 1823- Volume(issue)/page/year: 1,1256,1980 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X4863 No. of Facilities: 27 (estimated) No. of Industries: 1 No. of Occupations: 1 No. of Employees: 642 (estimated) No. of Female Employees: 346 (estimated)

 Safety Information

Symbol GHS07 GHS08
GHS07, GHS08
Signal Word Warning
Hazard Statements H317-H361
Precautionary Statements P280
Personal Protective Equipment Eyeshields;Faceshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges
Hazard Codes Xi:Irritant
Risk Phrases R36/37/38
Safety Phrases S36/37-S37/39-S26
RIDADR NONH for all modes of transport
WGK Germany 2
RTECS UY0550000
HS Code 2933990090

 Synthetic Route

 Customs

HS Code 2933990090
Summary 2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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