Related Searches: Cialis

Cialis(CAS No. 171596-29-5)

Cialis C22H19N3O4 (cas 171596-29-5) Molecular Structure

171596-29-5 Structure

Identification and Related Records

【CAS Registry number】
Pyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione,6-(1,3-benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-2-methyl-, (6R-trans)-
GF 196960
Tadalafil [USAN]
【Molecular Formula】
C22H19N3O4 (Products with the same molecular formula)
【Molecular Weight】
【Canonical SMILES】
【Isomers smiles】
【MOL File】

Chemical and Physical Properties

Off-White Cyrstalline Solid
1.51 g/cm3
【Melting Point】
【Boiling Point】
679.1oC at 760 mmHg
5.29E-13mmHg at 25°C
【Refractive Index】
【Flash Point】
In water, 220 mg/L at 25 deg C /Estimated/
【Computed Properties】
Molecular Weight:389.40396 [g/mol]
Molecular Formula:C22H19N3O4
H-Bond Donor:1
H-Bond Acceptor:4
Rotatable Bond Count:1
Tautomer Count:4
Exact Mass:389.137556
MonoIsotopic Mass:389.137556
Topological Polar Surface Area:74.9
Heavy Atom Count:29
Formal Charge:0
Isotope Atom Count:0
Defined Atom Stereocenter Count:2
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:4
Feature 3D Donor Count:1
Feature 3D Cation Count:1
Feature 3D Ring Count:6
Effective Rotor Count:2.4
Conformer Sampling RMSD:0.6
CID Conformer Count:6

Safety and Handling


The most common side effects of tadalafil?are: are headache, indigestion, flushing,back pain, muscle aches and stuffy or runny nose. These side effects reflect the ability of PDE5 inhibition to vasodilate (cause blood vessels to widen), these usually go away after a few hours. Back pain and muscle aches?maybe occur 12 to 24 hours after taking the drug,and the symptom usually disappears after 48 hours.

Oral: Tablets, film-coated: 5 mg (Cialis), (Lilly ICOS); 10 mg (Cialis), (Lilly ICOS); 20 mg (Cialis), (Lilly ICOS).
【Exposure Standards and Regulations】
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl tadalafil, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.

?Tadalafil? (CAS NO.171596-29-5) is the main raw materials of Cialis,compare with?Sildenafil,Tadalafil have less side effects, after taking two days,30% of people have muscles ache feeling (mainly waist and legs). It is also called as Tadalafil [USAN]?; (6R,12aR)-2,3,6,7,12,12a-Hexahydro-2-methyl-6-(3,4-(methylenedioxy)phenyl) pyrazino(1',2':1,6)pyrido(3,4-b)indole-1,4-dione ; (6R,12aR)-2,3,6,7,12,12a-Hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)pyrazino(1',2':1,6)pyrido(3,4-b)indole-1,4-dione ; (6R-trans)-6-(1,3-Benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-2-methyl-pyrazino(1',2':1,6)pyrido(3,4-b)indole-1,4-dione ; Adcirca ; Cialis ; Tadalafil ; Tadalafil Lilly ;Pyrazino(1',2':1,6)pyrido(3,4-b)indole-1,4-dione, 6-(1,3-benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-2-methyl-, (6R,12aR)- ; Pyrazino(1',2':1,6)pyrido(3,4-b)indole-1,4-dione, 6-(1,3-benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-2-methyl-, (6R-trans)- .

【Octanol/Water Partition Coefficient】
log Kow = 1.42 /Estimated/
【Disposal Methods】
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Use and Manufacturing


Used for the treatment of erectile dysfunction. A phosphodiesterase 5 inhibitor

Biomedical Effects and Toxicity

【Pharmacological Action】
- Compounds that specifically inhibit PHOSPHODIESTERASE 5.
- Drugs used to cause dilation of the blood vessels.
【Therapeutic Uses】
Tadalafil is indicated for the treatment of erectile dysfunction. /Included in US product labeling/
【Biomedical Effects and Toxicity】
Tmax: 30 minutes to 6 hours (median 2 hours). Absolute bioavailability has not been determined; rate and extent of absorption are not influenced by food.
Volume of distribution: 63 L; indicating distribution into tissues. Less than 0.0005% of administered dose was found in the semen of healthy subjects. 94% protein bound.
Over a dose range of 2.5 to 20 mg, tadalafil exposure (AUC) increases proportionally with dose in healthy subjects. Steady-state plasma concentrations are attained within 5 days of once-daily dosing, and exposure is approximately 1.6-fold greater than after a single dose.
Elimination: Mean oral clearance: 2.5 L per hour. Fecal: 61%. Urine: 36%.
Tadalafil and/or its metabolites crosses the placenta, resulting in fetal exposure in rats.
It is not known whether tadalafil is distributed into human breast milk. However, tadalafil and/or its major metabolites were secreted into the milk of lactating rats at concentrations approximately 2.4-fold greater than found in the plasma. Following a single-oral dose of 10 mg per kg, approximately 0.1% of the total radioactive dose was distributed into the milk within 3 hours.
Healthy male subjects (65 years of age and older) had a lower oral clearance of tadalafil, resulting in 25% higher exposure (AUC) with no effect on Cmax relative to that observed in healthy subjects 19 to 45 years of age; no dose adjustment is warranted based on age alone.
In clinical pharmacology studies, tadalafil exposure (AUC) in subjects with mild or moderate hepatic impairment (Child-Pugh Class A or B) was comparable to healthy subjects when a dose of 10 mg was administered; there are no available data for doses higher than 10 mg of tadalafil in patients with hepatic impairment; insufficient data are available for subjects with severe hepatic impairment (Child-Pugh Class C); dose adjustment needed for mild to moderate hepatic impairment; use in patients with severe impairment is not recommended.
In clinical pharmacology studies using single-dose tadalafil (5 to 10 mg), tadalafil exposure (AUC) doubled in subjects with mild (creatinine clearance 51 to 80 mL/min) or moderate (creatinine clearance 31 to 50 mL/min) renal insufficiency. In subjects with end-stage renal disease on hemodialysis, there was a two-fold increase in Cmax and 2.7- to 4.1-fold increase in AUC following single-dose administration of 10 or 20 mg tadalafil. Exposure to total methylcatechol (unconjugated plus glucuronide) was 2- to 4-fold higher in subjects with renal impairment, compared to those with normal renal function. Hemodialysis (performed between 24 and 30 hours post-dose) contributed negligibly to tadalafil or metabolite elimination.
In male patients with diabetes mellitus after a 10 mg tadalafil dose, exposure (AUC) was reduced approximately 19% and Cmax was 5% lower than observed in healthy subjects.
... Differences in pharmacokinetic properties among the PDE5 inhibitors include the fact that sildenafil and vardenafil have a shorter duration of action (approximately 4 hr) compared with the longer period of responsiveness observed with tadalafil (up to 36 hr). In addition, in the presence of high-fat food, absorption of sildenafil and vardenafil may be delayed; however, the rate and extent of tadalafil absorption are unaffected by high-fat food. [Seftel AD; Clin Cardiol 27 (4 Suppl 1): I14-19 (2004)] PubMed Abstract

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 53,000(SRC), determined from a structure estimation method(2), indicates that tadalafil is expected to be immobile in soil(SRC). Volatilization of tadalafil from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 5.0X10-18 atm-cu m/mole(SRC), determined by a fragment constant estimation method(3). Tadalafil is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.2X10-14 mm Hg(SRC), determined from a fragment constant method(4). Biodegradation data were not available(SRC, 2005).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 53,000(SRC), determined from a structure estimation method(2), indicates that tadalafil is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 5.0X10-18 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 2.5(SRC), from an estimated log Kow of 1.42(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data were not available(SRC, 2005).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), tadalafil, which has an estimated vapor pressure of 2.2X10-14 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 tadalafil may be removed from the air by wet and dry deposition(SRC).

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